Name: 17136-36-6|2-(Benzylamino)acetic acid|98%
Brand: Ambeed
SKU: A155349
Price: 9.0 USD
Availability: InStock
Rating: 96 (27 reviews)

1
[ 17360-47-3 ]
[ 17136-36-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1954,p. 1015
[2]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 203 - 206

2
[ 17136-36-6 ]
[ 6344-41-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; NaNO₂
	With hydrogenchloride; NaNO₂
	With hydrogenchloride; NaNO₂

	With hydrogenchloride; NaNO₂ for 2h;
	With hydrogenchloride; NaNO₂ In lithium hydroxide monohydrate at 0℃; for 1h;
	With isopentyl nitrite In 1,2-dimethoxyethane at 20℃; for 3h;
	With isopentyl nitrite In 1,2-dimethoxyethane at 30℃; for 2h;	217.217F Example 217F: 3-benzyl-3H-1,2,3-oxadiazol-1-ium-5-olate Behind a blast shield, to a solution of 2-(benzylamino)acetic acid (250 mg, 1.51 mmol) in 1,2-dimethoxyethane (7.0 mL) under nitrogen was added isoamyl nitrite (0.204 mL, 1.51 mmol). The reaction mixture stirred for 2 hours and was concentrated in vacuo (water bath at 30 °C to prevent decomposition). The crude residue was dispersed in dichloromethane:isohexane (1:15), concentrated in vacuo, and triturated using isohexane to afford 2-(benzyl(nitroso)amino)acetic acid.
	With isopentyl nitrite In 1,2-dimethoxyethane for 2h; Inert atmosphere;	217F Example 217F: 3-benzyl-3H-1,2,3-oxadiazol-1-ium-5-olate Behind a blast shield, to a solution of 2-(benzylamino)acetic acid (250 mg, 1.51 mmol) in 1,2-dimethoxyethane (7.0 mL) under nitrogen was added isoamyl nitrite (0.204 mL, 1.51 mmol). The reaction mixture stirred for 2 hours and was concentrated in vacuo (water bath at 30 °C to prevent decomposition). The crude residue was dispersed in dichloromethane:isohexane (1:15), concentrated in vacuo, and triturated using isohexane to afford 2-(benzyl(nitroso)amino)acetic acid. Behind a blast shield, to a solution of 2-(benzyl(nitroso)amino)acetic acid (294 mg, 1.51 mmol) in dichloromethane (7.00 mL) at 0 °C under nitrogen was added trifluoroacetic anhydride (0.214 mL, 1.51 mmol) dropwise. The reaction mixture was warmed to ambient temperature and stirred for 1.5 hours. Then water (7 mL) was added and the excess trifluoroacetic anhydride was quenched with sodium hydrogen carbonate. The phases were separated, and the aqueous layer was further extracted with dichloromethane (10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude amorphous solid, which was dispersed in dichloromethane:isohexane (1:15). This solution was then concentrated in vacuo to afford the title intermediate (202 mg, 1.03 mmol, 68% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.47 (dd, J = 5.0, 2.0 Hz, 3H), 7.41 - 7.35 (m, 2H), 6.17 (s, 1H), 5.35 (s, 2H).

Reference： [1]Eade; Earl [Journal of the Chemical Society, 1948, p. 2307,2309] Baker; Ollis; Poole [Journal of the Chemical Society, 1949, p. 307,314]
[2]Pollak,G. et al. [Journal of Medicinal Chemistry, 1964, vol. 7, p. 220 - 224]
[3]Farkas,J. et al. [Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 1434 - 1437]
[4]Gribble, Gordon W.; Hirth, Bradford H. [Journal of Heterocyclic Chemistry, 1996, vol. 33, # 3, p. 719 - 726]
[5]Location in patent: experimental part Fang, Yuesi; Wu, Chunrui; Larock, Richard C.; Shi, Feng [Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 8840 - 8851]
[6]Brown, Andrew W.; Fisher, Matthew; Tozer, Gillian M.; Kanthou, Chryso; Harrity, Joseph P. A. [Journal of Medicinal Chemistry, 2016, vol. 59, # 20, p. 9473 - 9488]
[7]Current Patent Assignee: SYGNATURE DISCOVERY LTD; ABBVIE INC; GOOGLE INC - WO2020/223538, 2020, A1 Location in patent: Page/Page column 372
[8]Current Patent Assignee: SYGNATURE DISCOVERY LTD; ABBVIE INC; GOOGLE INC - WO2022/94244, 2022, A1 Location in patent: Page/Page column 411; 413

3
[ 17136-36-6 ]
[ 108994-30-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With phosphorus pentachloride In toluene at 20℃; for 6h;	5 Example 5: Synthesis of the compound of formula (IV) in which R2 is hydrogen and X is chlorine To a suspension of PCI5 ( 1.51 g, 7.25 mmol) in Toluene (30 ml, 30 V) was added benzyl-glycine (1 g, 6.05 mmol). The reaction mixture was stirred at r.t. for 6h. To the obtained reaction mixture was filtered and the obtained solid was washed with DCM (10 ml_) for two times. The obtaining solid was dried on vacuum to give product (IV) hydrochloride salt (1.25 g, 93% yield) as a white solid.
	With phosphorus pentachloride; acetyl chloride

Reference： [1]Current Patent Assignee: HOLDING F.I.S. S.P.A. - WO2018/145860, 2018, A1 Location in patent: Paragraph 00141
[2]Mannich; Kuphal [Chemische Berichte, 1912, vol. 45, p. 319]

4
[ 67-56-1 ]
[ 17136-36-6 ]
[ 17136-35-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride In 1,4-dioxane	9.1 Step 1 : Methyl 2-(benzylamino)acetate hydrochloride (27). To a N-benzyl glycine 26 (500 mg, 3.0 mmol) in MeOH (6 mL) was added 4M solution of HCl in dioxane (4 mL) and stirred overnight. The reaction mixture was concentrated to afford compound 27 (649mg, 99%) as a white solid. The crude compound was carried forward without further purification. LRMS (ESI): (calc) 179.2 (found) 180.1(MH)+.
	With thionyl chloride
	With hydrogenchloride In 1,4-dioxane at 20℃; for 20h;

Reference： [1]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2008/122115, 2008, A1 Location in patent: Page/Page column 52
[2]Hardegger; Szabo; Liechti; Rostetter; Zankowska-Jasinska [Helvetica chimica acta, 1968, vol. 51, # 1, p. 78 - 85]
[3]Pulido, Daniel; Albericio, Fernando; Royo, Miriam [Organic Letters, 2014, vol. 16, # 5, p. 1318 - 1321]

5
[ 50-00-0 ]
[ 17136-36-6 ]
[ 37429-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid
	In formic acid at 70℃; for 5h;	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70° C., the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30×100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A=90% water, 10% methanol, 0. 1% TFA, B=10% water, 90% methanol, 0. 1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 179.22; Found: 180.20 (M+H)+.

Reference： [1]Rowley,G.L.; Kenyon,G.L. [Journal of Heterocyclic Chemistry, 1972, vol. 9, p. 203 - 206]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/44379, 2008, A1 Location in patent: Page/Page column 47

6
[ 420-04-2 ]
[ 17136-36-6 ]
[ 35404-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide
	Stage #1: N-benzylglycine With sodium chloride In water at 20℃; for 0.166667h; Stage #2: CYANAMID With ammonia In water at 20℃; for 97h;	1 Example 1. Production of phenylcreatine N-benzylglycine weighing 429 mg, and 0.5 ml of distilled water were mixed in a round-bottom flask of 10 ml volume. Then 152 mg of NaC1 were added to the mixture. Further, using a magnetic stirrer the mixture was stirred at room temperature for 10 minutes. In a small glass 206 mg of cyanamide and 0.2 ml of distilled water were added. Then a drop of solution of ammonia was added in catalytic quantities. The mixture was quickly mixed by gentle inverting, and then a mixture of cyanamide was added to a mixture of N-benzylglycine. The resulting mixture was stirred for one hour at room temperature. After 96 hours of incubation at room temperature and normal atmospheric pressure the product, namely phenylcreatine, N-benzyl-N-carbamimidoyl glycine, was precipitated. The crystals were transferred to a clean container with a volume of 10 ml.Purification of the sample was performed by recrystallization with the use of 1-2 ml of boiling distilled water. Then the solution was cooled to until its temperature became a room one. Then the solution was cooled on an ice bath for five minutes and dried in vacuum.The product was received also by incubation at higher temperatures up to 65°C, it was crystallized after from 24 hours to a week. If phenylcreatine remained in the solution, the solution was filtered until the dry crystals of the substance were discovered, vacuum filtration was used. The output of phenylcreatine ultimately amounted to 65-80%. Mass spectrum, found: mlz: MYR 207.2. Calculated: M 209.

Reference： [1]Rowley,G.L. et al. [Journal of the American Chemical Society, 1971, vol. 93, p. 5542 - 5551]
[2]Current Patent Assignee: ALEKSEEV; DUKHOVLINOV; BAIGUZIN - WO2018/135977, 2018, A1 Location in patent: Paragraph 0069; 0070; 0071; 0072

7
[ 67-56-1 ]
[ 17136-36-6 ]
[ 53386-64-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; In methanol; at 0℃; for 18h;	To a stirred solution of N-benzylglycine (820 mg, 4 mmol) and methanol (8 mL) was added thionyle chloride (2 mL) dropwise at 0 C. The mixture was stirred for 18 h. Then the solvent was evaporated under reduced pressure to give the compound benzylamino-acetic acid methyl ester as a white solid. Yield 100%. 1H NMR (DMSO-d6) delta ppm: 7.55-7.58 (m, 2H), 7.41-7.43 (m, 3H), 4.16 (s, 2H), 3.99 (s, 2H), 1.72 (s, 3H). tR,LCMS = 2.01 min; Purity 99%; MS (ESI+): m/z = 180 (M + H)+.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 90,p. 547 - 567
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 1267 - 1277
[3]Medicinal Chemistry Research,2013,vol. 22,p. 3918 - 3933

8
[ 50-00-0 ]
[ 141-32-2 ]
[ 17136-36-6 ]
[ 17012-21-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 4079 - 4090

9
[ 50-00-0 ]
[ 17136-36-6 ]
[ 122079-50-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	In benzene at 55℃;
	In benzene at 55℃; for 2h; Yield given;

Reference： [1]Bureau, R.; Mortier, J.; Joucla, M. [Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 584 - 596]
[2]Joucla, Marc; Mortier, Jacques [Bulletin de la Societe Chimique de France, 1988, # 3, p. 579 - 583]

10
[ 6436-90-4 ]
[ 17136-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water for 1h; Heating;
	With hydrogenchloride; sodium hydroxide 1.) aq. EtOH, r.t., 1 h: 2.) pH 7; Multistep reaction;
	With sodium hydroxide for 0.666667h; Heating;

	With sodium hydroxide In methanol at 20℃; for 0.5h;
	Multi-step reaction with 2 steps 2: aq. NaOH
	With hydrogenchloride; sodium hydroxide In water	9 EXAMPLE 9 EXAMPLE 9 Ethyl N-benzlglycinate is saponified in situ. An aqueous 30% strength NaOH solution (0.5 l=5 moles) and water (1 l) are mixed into this solution, ethyl N-benzylglycinate (965 g) is poured gradually over one hour. The temperature rises to 45° C. The ethanol is distilled off, the residue is cooled and a 6N aqueous hydrochloric acid solution (0.82 l) is added. The N-benzylglycine precipitates.
	In water	1.d d) d) N-Benzylglycine STR16 225.8 g (1.17 mol) of N-benzylglycine ethyl ester (J. Am. Chem. Soc. 72, 1238 (1950)) are heated under reflux overnight in 600 ml of water. Product which has crystallized out is filtered off with suction and the filtrate is extracted once with tert.-butyl methyl ether. The aqueous phase is concentrated and the crystals obtained are dried over phosphorus pentoxide in a desiccator together with the product filtered off. Yield: 184 g (95% of theory). Melting point: 199° C.
	With sodium hydroxide In 1,4-dioxane; methanol at 20℃; for 0.5h;

Reference： [1]McIntosh, John M.; Thangarasa, Rasiah; Foley, Nancy K.; Ager, David J.; Froen, Diane E.; Klix, Russell C. [Tetrahedron, 1994, vol. 50, # 7, p. 1967 - 1974]
[2]Kanemasa, Shuji; Sakamoto,Kazushige; Tsuge, Otohiko [Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 6, p. 1960 - 1968]
[3]Gribble, Gordon W.; Hirth, Bradford H. [Journal of Heterocyclic Chemistry, 1996, vol. 33, # 3, p. 719 - 726]
[4]Weber, Dirk; Berger, Claudia; Eickelmann, Peter; Antel, Jochen; Kessler, Horst [Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1918 - 1930]
[5]Hardegger; Szabo; Liechti; Rostetter; Zankowska-Jasinska [Helvetica chimica acta, 1968, vol. 51, # 1, p. 78 - 85]
[6]Current Patent Assignee: Lacroix; Guy - US4921991, 1990, A
[7]Current Patent Assignee: BAYER AG; THOMOND MOCKLER - US5071999, 1991, A
[8]Jahnsen, Rasmus D.; Frimodt-Møller, Niels; Franzyk, Henrik [Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7253 - 7261]

11
[ 3987-53-9 ]
[ 50-00-0 ]
[ 17136-36-6 ]
[ 100-52-7 ]
[ 124-40-3 ]
[ 103-67-3 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 826 - 832
[2]Helvetica Chimica Acta,1980,vol. 63,p. 1748 - 1749

12
[ 50-00-0 ]
[ 17136-36-6 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1988,p. 579 - 583
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 233 - 241

13
[ 24424-99-5 ]
[ 17136-36-6 ]
[ 76315-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triethylamine; In dichloromethane;	10A. (Benzyl-tert-butoxycarbonyl-amino)-acetic acid To 2-(benzylamino)acetic acid, HCl (3 g, 14.88 mmol) in DCM (40 mL) was added di-tert-butyl dicarbonate (3.25 g, 14.88 mmol) and TEA (6.22 mL, 44.6 mmol) and stirred for 6 days. The reaction was partitioned with DCM/dil HCl and extracted with DCM (3*20 mL). Combined organic layers were washed with water (20 mL), brine (20 mL) and dried (MgSO4) to afford 10A and containing some triethylamine hydrochloride impurity (5 g, 125%) as a clear colorless oil. 1H NMR (400 MHz, CDCl3) delta 1.38-1.46 (d, 9H), 3.71 (s, 1H), 3.86 (s, 1H), 4.54 (d, J=12.38 Hz, 2H), 7.07-7.37 (m, 5H). Used without further purification.
40.70 g	In tetrahydrofuran; water; for 6.5h;	To a suspension of /V-benzylglycine (24.3 g, 147 mmol) in THF:water (1 :1 , 500 mL) was added Boc-anhydride (33.7 g, 154 mmol). After 6.5 h the mixture was diluted with TBME (250 mL) and citric acid (33 g) was added until pH = 4. After 10 min of stirring, the phases were separated and the organic phase was washed with brine (250 ml). The aqueous layer was washed with TBME (2x100 ml) and the combined organic phases were dried over Na2S04, filtered then concentrated in vacuo (45C), affording the title compound (40.70 g) as a colorless oil, which began to crystallize upon standing. HPLC: 99.7% by UV, LCMS: Rt = 0.94 min, m/z = 264.3 (M-H), Method LCMS_ 2_MIN_FINAL_ANALYSIS. 1H NMR (600 MHz, DMSO-c/6)* delta 12.62 (br s, 1 H), 7.44-7.09 (m, 5 H), 4.41 (d, J = 8.1 Hz, 2 H) 1 .44-1 .24 (m, 9 H) 3.89-3.67 (m, 2 H). *As a mixture with 0(Boc)2 (ca. 9%).
	With triethylamine; In water; for 3h;	FIG. 7 - Step F. A 500-mL round-bottom flask was charged with N- benzylglycine (10.0 mmol), a water solution (100 mL) containing triethylamine (4.18 mL, 30.0 mmol, 3 equiv.; FW: 101.19 g/mol), and a teflon-coated stir bar. Di-/er/-butyl dicarbonate (2.18 g, 10.0 mmol, 1 equiv.; FW: 218.25 g/mol) was added and the solution was stirred for 3 h. The reaction mixture was poured into aqueous HC1 (1N, 30 mL) and extracted with ethyl acetate (3X100 mL). The organic layer was washed with water (1X100 mL) and brine (2X50 mL), dried over MgS04, filtered, and concentrated under reduced pressure to obtain product as white solid (93%).

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10664 - 10671
[2]Polish Journal of Chemistry,2002,vol. 76,p. 823 - 830
[3]Synthetic Communications,1994,vol. 24,p. 2429 - 2435
[4]Acta Crystallographica, Section C: Crystal Structure Communications,1998,vol. 54,p. 1164 - 1165
[5]Patent: US2010/16316,2010,A1 .Location in patent: Page/Page column 63
[6]Patent: WO2018/60926,2018,A1 .Location in patent: Paragraph 00203
[7]Patent: WO2020/92996,2020,A1 .Location in patent: Paragraph 00076

14
[(Z)-Benzylimino]-acetic acid [ No CAS ]
[ 17136-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol for 12h;

Reference： [1]Mouna; Nguyen; Rage; Xie; Nee; Mazaleyrat; Wakselman [Synthetic Communications, 1994, vol. 24, # 17, p. 2429 - 2435]

15
[ 7662-76-2 ]
[ 17136-36-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 1h;

Reference： [1]Alezra, Valérie; Bouchet, Céline; Micouin, Laurent; Bonin, Martine; Husson, Henri-Philippe [Tetrahedron Letters, 2000, vol. 41, # 5, p. 655 - 658]

16
[ 628-30-8 ]
[ 17136-36-6 ]
1-benzyl-3-propyl-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In 1,2-dichloro-ethane at 170℃; for 0.0833333h;

Reference： [1]Öhberg; Westman [Synlett, 2001, # 12, p. 1893 - 1896]

17
[ 17136-36-6 ]
[ 1544-68-9 ]
1-benzyl-3-(4-fluorophenyl)-2-sulfanylideneimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In 1,2-dichloro-ethane at 170℃; for 0.0833333h;

Reference： [1]Öhberg; Westman [Synlett, 2001, # 12, p. 1893 - 1896]

18
[ 17136-36-6 ]
[ 3288-04-8 ]
1-benzyl-3-(2-methoxy-phenyl)-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In 1,2-dichloro-ethane at 170℃; for 0.0833333h;

Reference： [1]Öhberg; Westman [Synlett, 2001, # 12, p. 1893 - 1896]

19
[ 100-52-7 ]
[ 56-40-6 ]
[ 17360-47-3 ]
[ 17136-36-6 ]

Reference： [1]Polish Journal of Chemistry,2002,vol. 76,p. 823 - 830

20
[ 17136-36-6 ]
[ 541-41-3 ]
[ 500224-59-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In tetrahydrofuran; water at 20℃;

Reference： [1]Herrero, M.Teresa; Tellitu, Imanol; Domínguez, Esther; Moreno, Isabel; SanMartín, Raúl [Tetrahedron Letters, 2002, vol. 43, # 46, p. 8273 - 8275] Correa, Arkaitz; Herrero, M. Teresa; Tellitu, Imanol; Domínguez, Esther; Moreno, Isabel; SanMartin, Raúl [Tetrahedron, 2003, vol. 59, # 36, p. 7103 - 7110]

21
[ 50-00-0 ]
[ 17136-36-6 ]
[ 623-91-6 ]
[ 92486-65-2 ]

Yield	Reaction Conditions	Operation in experiment
70.3%	In toluene at 105℃; for 18h; Heating / reflux;	1.1 Fumaric acid diethylester (21.6 g; 0.126 mol) is dissolved in toluene (900 ml) and heated at 105 °C. A mixture of N-benzylglycine (25 g; 0.151 mol) and paraformaldehyde (25.36 g; 0.844 mol) is added in 4 g portions to the refluxing solution. After completion of the addition the mixture is heated for 18 h at 105°C. The mixture is then evaporated to dryness and suspended in n-hexane. The insoluble material is filtered off and the remaining solution is evaporated to dryness. The crude product is used for the next step without further purification. Yield: 32.5 g (70.3 %), ESI-MS : m/z = 306 [M+H]+
	In toluene Heating;

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2005/92881, 2005, A1 Location in patent: Page/Page column 18; 29
[2]Rodriguez Sarmiento, Rosa Maria; Wirz, Beat; Iding, Hans [Tetrahedron Asymmetry, 2003, vol. 14, # 11, p. 1547 - 1551]

22
[ 6780-38-7 ]
[ 17136-36-6 ]
{Benzyl-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetyl]-amino}-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: N-benzylglycine With magnesium oxide In water at 25℃; for 4h; Stage #2: N-phthaloylglycine chloride In 1,4-dioxane; water at 25℃; for 2h;

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

23
[ 50-00-0 ]
[ 24393-59-7 ]
[ 17136-36-6 ]
(3S,4R)-1-Benzyl-4-(2-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In toluene at 110℃; for 8h;

Reference： [1]Viranyi, Andrea; Nyerges, Miklos; Blasko, Gabor; Toeke, Laszlo [Synthesis, 2003, # 17, p. 2655 - 2660]

24
[ 17136-36-6 ]
[ 6590-95-0 ]
1-benzyl-3-(2,6-dichloro-phenyl)-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In chloroform for 18h; Heating;

Reference： [1]Elokdah, Hassan; Sulkowski, Theodore S.; Abou-Gharbia, Magid; Butera, John A.; Chai, Sie-Yearl; McFarlane, Geraldine R.; McKean, Mar-Lee; Babiak, John L.; Adelman, Steven J.; Quinet, Elaine M. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 681 - 695]

25
[ 17136-36-6 ]
[ 607740-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C
	Multi-step reaction with 3 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

26
[ 17136-36-6 ]
[ 607740-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C
	Multi-step reaction with 5 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C
	Multi-step reaction with 3 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

27
[ 17136-36-6 ]
[ 607741-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C
	Multi-step reaction with 4 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C
	Multi-step reaction with 2 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

28
[ 17136-36-6 ]
[ 607740-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 9: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C
	Multi-step reaction with 7 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C
	Multi-step reaction with 5 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C

Multi-step reaction with 3 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[4]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

29
[ 17136-36-6 ]
4,7,10,13-tetrabenzyl-15-hydroxy-1,4,7,10,13-pentaaza-tricyclo[13.7.0.0^16,21]docosa-16,18,20-triene-3,6,9,12,22-pentaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 9: 70 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation
	Multi-step reaction with 7 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 7: 70 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation
	Multi-step reaction with 5 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 5: 70 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

30
[ 17136-36-6 ]
[ 607741-04-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C
	Multi-step reaction with 6 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C
	Multi-step reaction with 4 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 83 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

31
[ 17136-36-6 ]
[ 607741-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C
	Multi-step reaction with 6 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C
	Multi-step reaction with 4 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C

Multi-step reaction with 2 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[4]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

32
[ 17136-36-6 ]
4,7,10,13,16-pentabenzyl-18-hydroxy-1,4,7,10,13,16-hexaaza-tricyclo[16.7.0.0^19,24]pentacosa-19,21,23-triene-3,6,9,12,15,25-hexaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 9: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 10: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 11: 61 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation
	Multi-step reaction with 9 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 9: 61 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation
	Multi-step reaction with 7 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 7: 61 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation

Multi-step reaction with 5 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C 5: 61 percent / nBu₄NOH / methanol / 1 h / 17 °C / UV-irradiation

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[4]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

33
[ 17136-36-6 ]
[ 607741-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 96 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 94 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 9: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 10: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C
	Multi-step reaction with 8 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 100 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 7: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 8: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C
	Multi-step reaction with 6 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 97 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 96 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 5: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 6: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C

Multi-step reaction with 4 steps 1: 98 percent / Et₃N / H₂O / 3 h / 25 °C 2: 92 percent / EEDQ / CH₂Cl₂ / 3 h / 25 °C 3: 91 percent / TFA / CH₂Cl₂ / 4 h / 25 °C 4: 81 percent / Et₃N / CH₂Cl₂; dioxane / 3 h / 25 °C

Reference： [1]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[2]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[3]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]
[4]Yoon, Ung Chan; Jin, Ying Xue; Oh, Sun Wha; Park, Chan Hyo; Park, Jong Hoon; Campana, Charles F.; Cai, Xiaolu; Duesler, Eileen N.; Mariano, Patrick S. [Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671]

34
[ 848593-58-8 ]
[ 17136-36-6 ]
[ 848593-60-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	In toluene at 110℃; for 48h;	43.C 1-Benzyl-6a-methyl-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic Acid Benzyl Ester EXAMPLE 43C 1-Benzyl-6a-methyl-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic Acid Benzyl Ester The product of Example 43B (3.0 g, 12.1 mmol) was treated with benzylaminoacetic acid (Aldrich, 2.0 g, 12.1 mmol) in toluene (50 mL) at 110° C. over 2 days. The toluene was removed under reduced pressure and the residue was purified by column chromatography (SiO2, 40% hexanes-ethyl acetate) to give the title compound (2.8 g, 8.0 mmol, 66% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.23 (s, 3H), 1.49-1.64 (m, 1H), 1.93-2.10 (m, 1H), 2.36-2.51 (m, 1H), 2.56-2.67 (m, 1H), 2.73-2.87 (m, 1H), 3.10 (d, J=11.5 Hz, 1H), 3.32-3.41 (m, 1H), 3.52 (d, J=13.2 Hz, 1H), 3.58-3.78 (m, 3H), 5.03-5.22 (m, 2H), 7.14-7.42 (m, 10H); MS (DCI/NH3) m/z 351 (M+H)+.
66%	In toluene at 110℃; for 48h;	20.C 1-Benzyl-6a-methyl-hexa hydro-pyrrolo[3,4-b]pyrrole-5-carboxylic Acid Benzyl Ester Example 20C 1-Benzyl-6a-methyl-hexa hydro-pyrrolo[3,4-b]pyrrole-5-carboxylic Acid Benzyl Ester The product of Example 20B (3.0 g, 12.1 mmol) was treated with benzylaminoacetic acid (Aldrich, 2.0 g, 12.1 mmol) in toluene (50 mL) at 110° C. over 2 days. The toluene was removed under reduced pressure and the residue was purified by column chromatography (SiO2, 40% hexanes-ethyl acetate) to give the title compound (2.8 g, 8.0 mmol, 66% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.23 (s, 3H), 1.49-1.64 (m, 1H), 1.93-2.10 (m, 1H), 2.36-2.51 (m, 1H), 2.56-2.67 (m, 1H), 2.73-2.87 (m, 1H), 3.10 (d, J=11.5 Hz, 1H), 3.32-3.41 (m, 1H), 3.52 (d, J=13.2 Hz, 1H), 3.58-3.78 (m, 3H), 5.03-5.22 (m, 2H), 7.14-7.42 (m, 10H); MS (DCl/NH3) m/z 351 (M+H)+.

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2005/65178, 2005, A1 Location in patent: Page/Page column 39
[2]Current Patent Assignee: ABBVIE INC - US2005/101602, 2005, A1 Location in patent: Page/Page column 33-34

35
[ 50-00-0 ]
[ 17136-36-6 ]
[ 762-42-5 ]
C₂₃H₂₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	In water; toluene for 14h; Heating / reflux; Dean Stark trap;	41.1 Formaldehyde (37 wt. % in water) was added dropwise over 3 h to a refluxing suspension of N-benzylglycine (10 g, 60.37 mmol) and dimethylacetylenedicarboxylate (3.7 mL, 30.19 mmol) in 200 mL of toluene. The resulting mixture stirred and heated to reflux for 14 h while water was continuously removed using a Dean Stark trap. The reraction misxture was cooled to RT and evaporated. The residue was purified by Si02 chromatography eluting with a hexane/EtOAc gradient (100 % EtOAc to 75/25) over 40 minutes with and 80 mL/min flow rate to afford 3.4 g (28%) of 122a: 'H NMR (CDC13) 8 2.71 (d, 2H, J= 9 Hz), 3.08 (d, 2H, J= 9 Hz ), 3.66 (s, 5H), 7.17-7.42 (m, 5H) ; MS (ES+) m/z 409 (M + H)+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2005/121145, 2005, A2 Location in patent: Page/Page column 171-172

36
[ 509083-46-9 ]
[ 100-97-0 ]
[ 17136-36-6 ]
(+/-)-4-((5S,9R)-7-benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-9-yl)benzonitrile [ No CAS ]
4-[(5S*,9S*)-7-benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; toluene at 140℃; for 72h;	1 A mixture of (E)-4-((l-(3,5-dichlorophenyl)-3-methyl-2, 5- dioxoimidazolidin-4-ylidene)methyl)benzonitrile (1.05g, 2.82 mmol), hexamethylenetetramine (0.395 g, 2.82 mmol), N-benzylglycine (1.17 g, 7.05 mmol), toluene (5 ml), and l-methyl-2-pyrrolidinone (NMP, 10 ml) was heated to 140°C. The extent of reaction was monitored by HPLC. After 72 hours, the reaction had stopped short of completion. The ratio of product to starting material ((E)-4-((l-(3,5- dichlorophenyl)-3 -methyl-2, 5 -dioxoimidazolidin-4-ylidene)methyl)benzonitrile) was 1.36: 1. Mass spectra of the mixture indicated the presence of the desired product. The mixture was washed with water and extracted into toluene. The impure product was obtained as an oil. Comparison of the product obtained to authentic material was made by HPLC. The ratio of the desired (5S, 9R) isomer to the undesired was 19:1.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2006/65908, 2006, A1 Location in patent: Page/Page column 65

37
[ 17136-36-6 ]
[ 624-48-6 ]
[ 87813-06-7 ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-ethyl-N,N-diisopropylamine; paraformaldehyde In ethyl acetate; toluene	22.a tert-Butyl (3R,4S)-3-[(hydroxyamino)carbonyl]-4-[({4-[(2-methyl-4-quinolinyl)methoxy]phenyl}sulfonyl)methyl]-1-pyrrolidinecarboxylate trifluoroacetate (22a) A solution of N-benzylglycine (12.39 g, 75 mmol), dimethyl maleate (6.26 g, 50 mmol), paraformaldehyde (4.5 g, 150 mmol) and DIEA (8.7 mL, 50 mmol) in toluene (100 mL) was stirred at reflux for 2 hours and concentrated. The residue was taken up in EtOAc. The solution was washed with brine 3*, dried (MgSO4) and concentrated. Column chromatography eluding with 50% EtOAc/hexanes provided dimethyl cis-1-benzyl-3,4-pyrrolidinedicarboxylate (4.8 g, 34%). MS (M+H)+=278.5.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2003/87890, 2003, A1

38
[ 17136-36-6 ]
[ 23165-44-8 ]
1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform; water; ethyl acetate	24 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one EXAMPLE 24 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one A mixture of N-benzyl glycine (8.7 g), 4-n-butylphenyl-isothiocyanate (8.55 g), triethyl amine (5.5 g) and chloroform (150 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (2*300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (11.4 g) as an off-white solid, m.p. 149°-151° C. Anal. Calcd. for. C20 H22 N2 OS: C, 70.97; H, 6.55; N, 8.28. Found: C, 70.81; H, 6.76; N, 8.32. Mass spectrum (EI, M.+) m/z 338.
	With triethylamine In chloroform; water; ethyl acetate	53 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one EXAMPLE 53 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one A mixture of N-benzyl glycine (8.7 g), 4-n-butylphenyl-isothiocyanate (8.55 g), triethyl amine (5.5 g) and chloroform (150 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (300 mL) and water (2*200 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (11.4 g) as an off-white solid, m.p. 149°-151° C. Anal. Calcd. for. C20 H22 N2 O S: C, 70.97; H, 6.55; N, 8.28. Found: C, 70.81; H, 6.76; N, 8.32. Mass spectrum (EI, M.+) m/z 338.

Reference： [1]Current Patent Assignee: PFIZER INC - US5861517, 1999, A
[2]Current Patent Assignee: PFIZER INC - US5554607, 1996, A

39
[ 17136-36-6 ]
[ 128740-03-4 ]
[ 132414-78-9 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	e) Ethyl 2-benzyl-2,7-diazabicyclo[3.3.0]octane-7-carboxylate STR17 42.8 g (0.25 mol) of ethyl N-allyl-N-(2-oxoethyl) -carbamate are heated under reflux overnight with 41.3 g (0.25 mol) of N-benzylglycine in 750 ml of toluene. The mixture is concentrated and the residue is distilled. Yield: 59.6 g (87% of theory). Boiling point: 140 C./0.09 mbar.

Reference： [1]Patent: US5071999,1991,A

40
[ 17136-36-6 ]
[ 128740-03-4 ]
C₁₆H₂₂N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2891 - 2894

41
[ 17136-36-6 ]
(S)-2-amino-butanamide [ No CAS ]
[ 1076190-08-3 ]

Yield	Reaction Conditions	Operation in experiment
58.9%	Stage #1: N-benzylglycine With triethylamine In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 0.416667h; Stage #2: (S)-2-amino-butanamide With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform-d1; N,N-dimethyl-formamide at 20 - 45℃;	1.1 In a three necked flask fitted with a magnetic stirrer and a reflux condenser, under inert atmosphere, triethylamine (69 ml_, 496 mmol) is added dropwise to a solution of (benzylamino)acetic acid a1 (50 g, 248 mmol) in a mixture of DMF (400 ml.) and CHCI3 (400 ml.) at 0 0C. The mixture is stirred at 0 0C for 10 minutes and at room temperature for 15 minutes. 1 H-1 ,2,3-benzotriazol-1-ol (36.9 g, 273 mmol), (2S)-2-aminobutanamide a2 (30.4 g, 298 mmol) and N,N'-dicyclohexylcarbodiimide (56.33 g, 273 mmol) are respectively added to the mixture, each one of them in solution of 250 ml. (or 300 ml.) of CHCI3/DMF (50/50 v/v). DMF (200 mL) is added and the mixture is heated at 45 0C for 4 h, and stirred at room temperature for 3 days. The mixture is partially concentrated (2/3 of solvent is removed) and again heated at 45 0C overnight. The whole solvent is removed under reduced pressure, the residue is dissolved in CH2CI2 and filtered. The organic phase is concentrated, the obtained residue is purified by chromatography on silicagel (CH2CI2ZC2H5OHZNH4OH 94/6/0.6 v/v/v) and recrystallized from AcOEt to afford (2S)-2- [(benzylamino)acetyl]amino}butanamide a3 (36.8 g). Yield: 58.9 %.1 H NMR δH (250 MHz, DMSO, ppm): 0.85 (t, 3 H), 1.5-1.8 (m, 2 H), 2.7 (s, 1 H), 3.15 (s, 2H), 3.7 (s, 2 H), 4.25 (m, 1 H), 7.0 (s, 1 H), 7.2-7.5 (m, 6 H), 7.9 (d, 1 H).

Reference： [1]Current Patent Assignee: UCB - WO2008/132139, 2008, A2 Location in patent: Page/Page column 55

42
[ 50-00-0 ]
[ 17136-36-6 ]
[ 76-05-1 ]
[ 1007880-03-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70° C., the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30×100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A=90% water, 10% methanol, 0.1% TFA, B=10% water, 90% methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 179.09; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine In formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water HPLC;	49 To a stirred solution of 2- (benzylamino) acetic acid (2.O g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol) . After five hours at 70 0C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl (methyl) -amino) acetic acid as its TFA salt (723118 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 {s, 2H) 4.34 (s, 2H) 7.29-7.68 (m,5H) . LCMS: Anal. Calcd. for: Ci0Hi3NO2 175.05; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine In formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 0C5 the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (XTERRA 30 X 100 mm, detection at 220 nm, flow rate 35 mL/rnin, 0 to 35% B over 8 min; A- 90% water, 10 % methanol, 0.1% TFA, B=I 0% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSOd6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29- 7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 175.05; Found: 180.20 (M+H)+

33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	Cap-49 To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 °C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (XTERRA 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. XH NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: Ci0H13NO2 179.09; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water RP-HPLC;	49 To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 °C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (XTERRA 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B= 10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 179.09; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 °C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. XH NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: Ci0H13NO2 179.09; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water reverse-phase preparative HPLC;	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 0C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: Ci0Hi3NO2 175.05; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	Cap-49To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 0C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A = 90% water, 10 % methanol, 0.1% TFA, B = 10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29 - 7.68 (m, 5H). LCMS: Anal. Calcd. for: Ci0H13NO2 179.22; Found: 180.20 (M+H)+.
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	49 To a stirred solution of 2-(benzylamino)acetie acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70° C., the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30×100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A=90% water, 10% methanol, 0.1% TFA, B=10% water, 90% methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 179.09; Found: 180.20 (M+H)+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2009/233925, 2009, A1 Location in patent: Page/Page column 34
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2010/120621, 2010, A1 Location in patent: Page/Page column 118; 119
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2010/138488, 2010, A1 Location in patent: Page/Page column 110
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2011/60000, 2011, A1 Location in patent: Page/Page column 151-152
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2011/59850, 2011, A1 Location in patent: Page/Page column 66
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2012/18325, 2012, A1 Location in patent: Page/Page column 64
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2008/144380, 2008, A1 Location in patent: Page/Page column 76
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2009/102318, 2009, A1 Location in patent: Page/Page column 72
[9]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2010/249190, 2010, A1 Location in patent: Page/Page column 41

43
[ 50-00-0 ]
[ 17136-36-6 ]
[ 623-91-6 ]
[ 1126794-79-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene at 105℃; for 17h; Heating / reflux;	5.16.16 To a mixture of diethyl fumarate (8 68g, 50 4mmol, Sigma-Aldϖch) and toluene (80OmL) at 1050C was added dropwise over Ih a mixture of formaldehyde, in the form of paraformaldehyde, (10 2g, 339mmol (based on formaldehyde monomer molecular weight), Sigma-Aldϖch) and 2-(benzylamino)acetic acid (12 2g, 60 5mmol, Sigma-Aldϖch) The resulting reaction mixture was refluxed for 16h in an apparatus comprising a Dean-Stark trap After concentration under reduced pressure, the residue was dissolved in hexanes, filtered, and concentrated under reduced pressure to provide a brown oil. Flash chromatography of the oil with a silica gel column eluting with 1 :5 EtOAc:hexanes provided 13 8g of the compound of formula FU as a colorless oil (yield 74%). The identity of the compound of formula FU, (3S,4S)-di ethyl l-benzylpyrrohdine-3,4- dicarboxylate, was confirmed using TLC and LC/MS.Compound FU: TLC (SiO2) 1 :1 EtOAc:hexanes: Rf=O 8 with UV detection, Dragendorff s reagent; LC/MS: /n/z=306 [M+H]+ (CaIc: 305).

Reference： [1]Current Patent Assignee: PURDUE PHARMA L.P. - WO2009/27820, 2009, A2 Location in patent: Page/Page column 235-236

44
[ 17136-36-6 ]
[ 7146-15-8 ]
[ 1019647-39-2 ]

Yield	Reaction Conditions	Operation in experiment
77%		Method 14; Methyl glycyl-D-valinate hydrochloride; N-Benzylglycin (500 mg, 3.03 mmol) was dissolved in 20 ml DCM. DIPEA (1.55 ml, 9.08 mmol) and TBTU (1.17 g, 3.63 mmol) were added and the suspension was stirred for 10 min. <strong>[7146-15-8]D-Valine methyl ester hydrochloride</strong> (510 mg, 3.03 mmol) was added during 5 min and the mixture was stirred over night. Water (ca 10 ml) was added and the aqueous phase was acidified to pH 4 using 0.3 M KHS04. The yellow organic phase was washed with 10 ml acidified water (KHS04) followed by water, dried and concentrated. The crude mixture was purified by chromatography on 50 g Si02 using a gradient from 20-80% EtOAc in hexane as eluent. The intermediate (650 mg, 77%), was dissolved in MeOH and 25 mg Pd/C (10 mol%) was added. The solution was hydrogenated at 1 atm over night. The solution was filtered over celite and concentrated. MeCN, 10 ml, was added and the mixture was heated to ca 60C. Pyridine hydrochloride (220 mg, 1.86 mmol) was added and the solution was slowly allowed to cool down. The solvent was removed under reduced pressure and the residue was recrystallized from 5 ml MeCN. The white solid was filtered off to yield the title compound in 360 mg (69%). lH-NMR (CD30D, 400 MHz) : 8 0.92 (dd, 6H), 2.07-2. 19 (m, 1H), 3.68 (s, 3H), 3.71 (s, 2H), 4. 37 (d, 1H).

Reference： [1]Patent: WO2005/61451,2005,A1 .Location in patent: Page/Page column 57

45
[ 858104-55-9 ]
[ 17136-36-6 ]
C₃₆H₃₁F₂N₃O₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3R,4R)-1-(4-fluorophenyl)-3-[(4-fluorobenzoyl)methylthio]-4-{4-[N-(carboxymethyl)carbamoylmethoxy]phenyl}azetidin-2-one With 4-methyl-morpholine; (1,1,1-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate In DMF (N,N-dimethyl-formamide) at 30℃; for 0.5h; Stage #2: N-benzylglycine In DMF (N,N-dimethyl-formamide) at 30℃; for 1h;	48 Example 48; N-[4-((2R, 3R)-1-(4-Fluorophenyl)-3-[2-(4-lluorophenyl)-2-hydroxyethyl] thio}-4- oxoazetidin-2-yl) phenoxy] acetyl} glycyl-N-benzylglycine; TBTU (0. 011 g, 0.034 mmol) was added to a solution of N-{ [4-((2R, 3R)-1-(4-fluorophenyl)- 3- { [2- (4-fluorophenyl)-2-oxoethyl] thio}-4-oxoazetidin-2-yl) phenoxy] acetyl} glycine (0.015 g, 0.028 mmol) and NMM (0.020 ml, 0.182 mmol) in DMF (2 ml) at 30°C. After 30 min, N- benzylglycine (0.005 g, 0.030 mmol, 98 %) was added and the mixture was stirred at 30°C for 1h. The reaction was quenched with water (0.2 ml) and the mixture was diluted with MeOH (2 ml). NaBH4 (0.015 g, 0.397 mmol) was added and the mixture was stirred for 10 min. Ammonium acetate buffer (0. 1M, 3 ml) was added and most of the methanol was removed under reduced pressure. The remaining solution was purified by preparative HPLC, using a gradient of 20-50% MeCN in 0. 1M ammonium acetate buffer as eluent. After freeze-drying, the title compound (0.010 g, 53 % yield) was obtained as a white solid. M/z : 690.0. 1H NMR (DMSO, 400 MHz) : 8 2.83-2. 94 (m, 2H), 3.91 (s, 1H), 3.98-4. 09 (m, 3H), 4.25-4. 29 (m, 1H), 4.50 (s, 2H), 4.54 (s, 1H), 4.62 (s, 1H), 4.68-4. 76 (m, 1H), 5.02-5. 07 (m, 1H), 6.92-7. 02 (m, 2H), 7.05-7. 40 (m, 15H), 8.14-8. 21 (m, 1H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2005/61452, 2005, A1 Location in patent: Page/Page column 91-92

46
[ 50-00-0 ]
[ 17136-36-6 ]
[ 1007880-03-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	With formic acid at 70℃; for 5h;	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 0C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-de) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: Ci0Hi3NO2 179.09; Found: 180.20 (M+H)*

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2010/17401, 2010, A1 Location in patent: Page/Page column 215

47
[ 17136-36-6 ]
[ 100-52-7 ]
[ 536-74-3 ]
N-benzyl-N-methyl-1,3-diphenylprop-2-yn-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: N-benzylglycine With copper(l) iodide In toluene for 0.166667h; Inert atmosphere; Stage #2: benzaldehyde; phenylacetylene In toluene at 130℃; Inert atmosphere;

Reference： [1]Bi, Hai-Peng; Teng, Qingfeng; Guan, Min; Chen, Wen-Wen; Liang, Yong-Min; Yao, Xiaojun; Li, Chao-Jun [Journal of Organic Chemistry, 2010, vol. 75, # 3, p. 783 - 788]

48
[ 17136-36-6 ]
[ 123-11-5 ]
[ 536-74-3 ]
[ 1206905-72-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: N-benzylglycine With copper(l) iodide In toluene for 0.166667h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde; phenylacetylene In toluene at 130℃; Inert atmosphere;

Reference： [1]Bi, Hai-Peng; Teng, Qingfeng; Guan, Min; Chen, Wen-Wen; Liang, Yong-Min; Yao, Xiaojun; Li, Chao-Jun [Journal of Organic Chemistry, 2010, vol. 75, # 3, p. 783 - 788]

49
N-[4-((2R,3R)-1-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycylglycine [ No CAS ]
[ 17136-36-6 ]
C₃₈H₃₄F₂N₄O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-[4-((2R,3R)-1-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycylglycine With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 30℃; for 0.5h; Stage #2: N-benzylglycine In N,N-dimethyl-formamide at 30℃; for 2.5h;	2 Example 2 iV-[4-((2R,3i?)-l-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4- oxoazetidin-2-yl)phenoxy]acetyl}glycylglycyl-yV-benzylgIycine EPO To a solution of iV-[4-((2i?,3i?)-l-(4-fluoroρhenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}- 4-oxoazetidin-2-yl)phenoxy]acetyl}glycylglycine (0.020 g, 0.033 ininol) and NMM (0.015 ml, 0.136 mmol) in DMF (2 ml) at 3O0C was added TBTU (0.015 g, 0.047 mmol). After 30min was N-benzylglycine (0.006 g, 0.036 mmol, 98 %) added and the mixture was stirred at 3O0C for 2h30min. The reaction was quenched by the addition of water (1 ml) and the resulting mixture was diluted with MeOH (2 ml). To this solution was added NaBH4 (0.020 g, 0.529 mmol) and the mixture was stirred for 10 min. The reaction was quenched by the addition of a 0. IM ammonium acetate buffer (3 ml) before most of the methanol was removed under reduced pressure. The remaining solution was purified by preparative HPLC, using a gradient of 20-50% MeCN in 0.1M ammonium acetate buffer as eluent. Freeze-drying of the pure fractions gave the title compound.Accurate mass: 747.2315 (M+l)+

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2006/137794, 2006, A1 Location in patent: Page/Page column 56-57

50
[ 50-00-0 ]
[ 17136-36-6 ]
[ 76-05-1 ]
2-(benzyl(methyl)-amino)acetic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: formaldehyd; N-benzylglycine In formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mniol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 700C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (XTERRA 30 X 100 mm, detection at 220 ran, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B=I 0% water, 90 % methanol, 0.1% TFA) provided the title compound 2- (benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSOd6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29- 7.68 (m, SH). LCMS: Anal. Calcd. for: C10H13NO2 179.09; Found: 180.20 (M+H)÷.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2010/138368, 2010, A1 Location in patent: Page/Page column 70

51
[ 7689-50-1 ]
[ 17136-36-6 ]

Reference： [1]Journal of Physical Chemistry A,2010,vol. 114,p. 2483 - 2488

52
[ 50-00-0 ]
[ 17136-36-6 ]
[ 234452-57-4 ]
C₂₇H₃₁N₂O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water; acetic acid for 5h; Reflux;	Phosphinomethylation of a secondary amino acid. General procedure: A phosphinic acid (3.0 mmol) and a secondary amino acid (6.0 mmol) were dissolved in a hot H2O/AcOH/HClconcd mixture (10:10:0.5 mL). Formaldehyde (36-38% aqueous solution, 30.0 mmol, 3.0 mL) was added dropwise to the stirred solution. After addition, the mixture was refluxed for 5-6 h and then cooled to room temperature. The precipitated solid was filtered and dried in the air. The benzyloxycarbonyl protection was removed as described above.

Reference： [1]Location in patent: experimental part Dziełak, Anna; Pawełczak, Małgorzata; Mucha, Artur [Tetrahedron Letters, 2011, vol. 52, # 24, p. 3141 - 3145]

53
[ 1631-26-1 ]
[ 17136-36-6 ]
[ 1220514-64-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1-benzyl-1H-pyrrole-2,5-dione; N-benzylglycine In toluene at 105℃; Large scale reaction; Stage #2: With formaldehyd; water In toluene at 105℃; Large scale reaction;

Reference： [1]Location in patent: experimental part Huang, Xiaojun; O'Brien, Erin; Thai, Felicia; Cooper, Gary [Organic Process Research and Development, 2010, vol. 14, # 3, p. 592 - 599]

54
[ 50-00-0 ]
[ 64-18-6 ]
[ 17136-36-6 ]
[ 76-05-1 ]
[ 1007880-03-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: formaldehyd; formic acid; N-benzylglycine at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	cap-49[00180] To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde (6.94 mL, 93.2 mmol). After five hours at 70 °C, the reaction mixture was concentrated under reduced pressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and further concentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC (XTERRA 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol, 0.1% TFA, B= 10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acid as its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34 (s, 2H) 7.29-7.68 (m, 5H). LC-MS: Anal. Calcd. for: C10H13NO2 179.09; found: 180.20 (M+H)+. -50

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2011/75439, 2011, A1 Location in patent: Page/Page column 61

55
[ 7677-24-9 ]
[ 17136-36-6 ]
[ 100-52-7 ]
[ 51643-97-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	In butan-1-ol at 200℃; for 0.166667h; Microwave irradiation; regioselective reaction;

Reference： [1]Das, Deepankar; Richers, Matthew T.; Ma, Longle; Seidel, Daniel [Organic Letters, 2011, vol. 13, # 24, p. 6584 - 6587]

56
[ 39603-24-2 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-83-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	In methanol at 100℃; for 0.333333h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

57
[ 317-20-4 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-84-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	In methanol at 100℃; for 0.333333h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

58
[ 17136-36-6 ]
[ 91-56-5 ]
andrographolide [ No CAS ]
[ 1415404-76-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

59
[ 608-05-9 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-77-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

60
[ 20780-76-1 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-79-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

61
[ 443-69-6 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-80-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

62
[ 39755-95-8 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-81-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

63
[ 17136-36-6 ]
[ 87-48-9 ]
andrographolide [ No CAS ]
[ 1415404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

64
[ 321-69-7 ]
[ 17136-36-6 ]
[ 1420354-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 157℃; for 2h;	General procedure: 6-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (20.8 g, 108 mmol) was suspended in DMSO (55 mL). The mixture was then placed on a preheated mantle (157 C). The mixture was stirred until dissolved. Sarcosine (32.0 g, 108 mmol) was added portionwise. Almost immediately effervescence was observed. The mixture was heated for 2 h then cooled to ca. 70 C then poured into water (300 mL). A suspension of a white powder formed which was collected by filtration and dried in vacuo (13.9 g, 59%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 821 - 826

65
[ 17136-36-6 ]
[ 1447816-71-8 ]
C₂₁H₁₉ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 100℃; Inert atmosphere;	General procedure for the synthesis of fused tetracyclic quinolines using ionic liquids General procedure: A mixture of 5-chloro-7-formyl-O-allyl-8-hydroxy quinoline 3a(1 mmol, 247 mg), sarcosine 4a (1.2 mmol, 107 mg) and ionic liquid [bmim]PF6 (5 mL) was taken in a round bottom flask under nitrogen atmosphere. The contents of the flask were stirred magnetically at 100 ± 2°C. The progress of the reaction was monitored by TLC in pet. ether-ethyl acetate (5:5) and visualization was accomplished in an iodine chamber. After completion of the reaction, the contents were neutralized with 10% aqueous sodium bicarbonate solution and extracted with ethyl acetate (3 10 mL). The solvent was removed under reduced pressure. The pasty mass thus obtained was extracted with diethyl ether (3 10 mL); the extract was dried over an hydrous sodium sulfate, and ether was distilled. The product was purified by column chromatography followed by crystallization with chloroform-hexane. The ionic layer was washed with water (3 5 mL) and kept for 2 h at80-85°C under reduced pressure for recycling.

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Maity, Arindam; Mondal, Shyamal; Mondal, Nirup B. [Tetrahedron Letters, 2013, vol. 54, # 32, p. 4339 - 4342]

66
[ 17136-36-6 ]
phenyl 2-(benzyloxy)-3-[(tert-butoxy)carbonyl](prop-2-en-1-yl)amino}-4-formyl-6-methyl-5-(trifluoromethoxy)benzoate [ No CAS ]
5-tert-butyl 7-phenyl (3aS,9bS)-1-benzyl-6-(benzyloxy)-8-methyl-9-(trifluoromethoxy)-1H,2H,3H,3aH,4H,5H,9bH-pyrrolo[3,2-c]quinoline-5,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In N,N-dimethyl-formamide at 100℃; for 6h;

Reference： [1]Sun, Cuixiang; Hunt, Diana K.; Chen, Chi-Li; Deng, Yonghong; He, Minsheng; Clark, Roger B.; Fyfe, Corey; Grossman, Trudy H.; Sutcliffe, Joyce A.; Xiao, Xiao-Yi [Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4703 - 4712]

67
[ 17136-36-6 ]
[ 84-65-1 ]
N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With formaldehyd In 1,4-dioxane; benzene for 3h; Reflux; Dean-Stark;

Reference： [1]Buev, Evgeny M.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y. [Organic Letters, 2016, vol. 18, # 8, p. 1764 - 1767]

68
[ 17136-36-6 ]
(2R,3S)-2-(3,4-dimethoxyphenyl)-3-((4R,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methoxymethoxy)propanal [ No CAS ]
(3aR,4S,5R,5aR,8bR)-6-benzyl-5-(3,4-dimethoxyphenyl)-4-(methoxymethoxy)-2,2-dimethyl-3a,5,5a,6,7,8b-hexahydro-4H-[1,3]dioxolo[4,5-e]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With triethylamine In toluene at 115℃; for 24h; Molecular sieve;	(3aR,4S,5R,5aR,8bR)-6-benzyl-5-(3,4-dimethoxyphenyl)-4-(methoxymethoxy)-2,2-dimethyl-3a,5,5a,6,7,8b-hexahydro-4H-[1,3]dioxolo[4,5-e]indole (14). To a mixture of N-Bn-glycine (82 mg, 0.49 mmol), TEA (87 μL, 0.63 mmol) and 4 Å molecular sieves in toluene (1.5 mL) was added 13 (47 mg, 0.12 mmol) dissolved in 0.5 mL toluene. The mixture was stirred at 115°C for 24h, cooled to room temperature and was added water. The aqueous layer was extracted with CH2Cl2, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (PE-EtOAc, 8:1) to afford 14 (18 mg, 30%) as a white solid. [α]25D= -16 (c = 1.0, CHCl3); 1H NMR (400 MHz, CDCl3)δ 7.25 -7.07 (m, 5H), 7.04 -6.76 (m, 3H), 5.59 (s, 1H, H-3), 4.86 (d, J=6.9 Hz, 1H, -CH2), 4.26 (d, J= 6.9 Hz, 1H, -CH2),4.13 (m, 2H, H-4, H-6), 3.89 -3.80 (m, 7H, -CH3, H-7a), 3.74 -3.66(m, 1H), 3.60(t, J= 9.4 Hz, 1H, H-5), 3.25 (d, J= 14.5 Hz, 1H),3.20 (d, J= 13.5 Hz, 1H), 3.10 (d, J= 13.1 Hz, 1H), 2.78 (t, J=9.9 Hz, 1H, H-7), 2.72 (s, 3H), 1.50 (s, 3H), 1.48 (s, 3H).13C NMR (100 MHz, CDCl3) δ 158.55, 149.38, 148.42, 140.14, 131.07, 129.55, 119.92,113.54, 111.76, 79.47, 77.20, 74.16, 72.26, 71.28, 60.71, 59.24, 55.92, 55.87,55.2, 29.68; HR ESI MS m/z Calcd forC28H36NO6 ([M+H]+) 482.25371, found 482.25364.

Reference： [1]Zhang, Wenxuan; Wang, Jiming; Luo, Xihuan; Meng, Xiangbao; Li, Zhongjun [Tetrahedron Letters, 2016, vol. 57, # 18, p. 1981 - 1984]

69
[ 17136-36-6 ]
[ 610-14-0 ]
[ 1843-50-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 4h;	Synthesis of 2-nitrobenzamide-aminoacid derivatives 15. General procedure: To a solution of commercially available N-benzylglycine14a, N-benzyl-L-alanine 14b, N-benzyl-L-valine 14c or N-benzyl-L-phenylalanine 14d3 (6.06 mmol) and Et3N (2.2 mL, 15.15 mmol) in a mixture of THF (10mL) and H2O (10 mL) was added 2-nitrobenzoyl chloride (1.35 g, 7.27 mmol) at 0 °C and the resulting mixture was allowed to stir at room temperature for 4 h. The reaction mixture was evaporated to remove THF, the aqueous residue was acidified (pH ~2) with con. HCl, and extracted with 10% MeOH/CHCl3.The organic extract was washed with brine, dried with anhydrousMgSO4 and concentrated. The crude compound was purified by trituration with CHCl3/n-pentane to give the protected β-ketomethyl esters 15a-d.

Reference： [1]Sorra, Kumaraswamy; Lai, Chin-Hung; Feng, Chun-Yen; Wu, Yang-Chang; Pusuluri, Srinivas; Mukkanti, Khagga; Chuang, Ta-Hsien [Tetrahedron Letters, 2016, vol. 57, # 43, p. 4842 - 4844]

70
[ 50-00-0 ]
[ 17136-36-6 ]
[ 76-05-1 ]
2-(benzyl(methyl)amino)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: formaldehyd; N-benzylglycine With formic acid at 70℃; for 5h; Stage #2: trifluoroacetic acid In methanol; water	Cap-49 To a stirred solution of 2-(benzylamino)acetic acid (2.0 g, 12.1 mmol) in formic acid (91 mL) was added formaldehyde(6.94 mL, 93.2 mmol). After five hours at 70 °C, the reaction mixture was concentrated under reducedpressure to 20 mL and a white solid precipitated. Following filtration, the mother liquors were collected and furtherconcentrated under reduced pressure providing the crude product. Purification by reverse-phase preparative HPLC(Xterra 30 X 100 mm, detection at 220 nm, flow rate 35 mL/min, 0 to 35% B over 8 min; A= 90% water, 10 % methanol,0.1 % TFA, B=10% water, 90 % methanol, 0.1% TFA) provided the title compound 2-(benzyl(methyl)-amino)acetic acidas its TFA salt (723 mg, 33%) as a colorless wax. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.75 (s, 3H) 4.04 (s, 2H) 4.34(s, 2H) 7.29-7.68 (m, 5H). LCMS: Anal. Calcd. for: C10H13NO2 179.09; Found: 180.20 (M+H)+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - EP2328865, 2017, B1 Location in patent: Paragraph 0411-0412

71
[ 1018593-81-1 ]
[ 17136-36-6 ]
2-(benzylamino)-1-(4-(3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl)piperidin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	30.1 Step 1: Preparation of 2-(benzylamino)- 1-(4-(3-(3,4-dimethoxyphenyl)- 1,2,4-oxadiazol-5-yI)piperidin- 1-yI)ethanone. To a stirred solution of 3-(3,4-dimethoxyphenyl)-5-(4-piperidyl)-1 ,2,4-oxadiazole (1 50 mg, 518 imol) in N,N-dimethylformamide (1 .50 mL) were added (2-(1 H-benzotriazol-1 -yl)-l ,1 3,3- tetramethyluronium hexafluorophosphate) (196 mg, 518 imol), N-ethyl-N-(propan-2-yl)propan-2-amine(201 mg, 1.56 mmol, 271 iL), and 2-(benzylamino)acetic acid (89 mg, 544 imol). The mixture wasstirred at 20 °C for 16 h and filtered, and the crude filtrate was purified directly by prep-HPLC (column:Luna 08 100x30 Slim; mobile phase: [water (10mM ammonium carbonate)-acetonitrile]; B%: 30%-60%,1 2 mm) to give 2-(benzylamino)-1 -[4-[3-(3,4-dimethoxyphenyl)-1 ,2,4-oxadiazol-5-yl]-1 -piperidyl]ethanone (48 mg, 110 limol, 21 %) as a yellow solid. 1 NMR (400MHz, METHANOL-d4) O7.65 (dd, J1 .8, 8.2 Hz, 1 H), 7.57 (d, J1 .8 Hz, 1 H), 7.40 - 7.30 (m, 4H), 7.28 - 7.22 (m, 1 H), 7.06 (d,J8.4 Hz, 1 H), 4.45 (br d, J1 3.7 Hz, 1 H), 3.94 - 3.83 (m, 7H), 3.78 (s, 2H), 3.57 - 3.44 (m, 2H), 3.40 - 3.33 (m, 1 H), 3.27 - 3.20 (m, 1 H), 3.01 (t, J1 1.2 Hz, 1 H), 2.17 (dd, J2.8, 13.3 Hz, 2H), 1.93 - 1.73 (m, 2H); LCMS (ESI) m/z: [M÷H] 437.3.

Reference： [1]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2018/81167, 2018, A1 Location in patent: Paragraph 124

72
[ 32315-10-9 ]
[ 17136-36-6 ]
N-benzyl-N-carboxyanhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In ethyl acetate for 4.67h;	16 Example 16: Synthesis of the compound of formula (II) in which Ri is Ethyl and R2 is Hydrogen, i.e. compound (ll-a) To a solution of triphosgene (3.6g, 0.4eq) in ethyl acetate (i.e. EtOAc) (200ml, 40V) was added N-Benzyl glycine (5g, 1 eq). Then a solution of triethylamine (3.37g, 1 .1 eq) in EtOAc (50ml, 10V) was added dropwise over a period of 40 min, and the mixture was stirred for another 4 h. The obtained reaction mixture was filtered and concentrate under vacuum to give the compound of formula (X-a) 3.64g, yield 63%, HPLC purity 96.43%. It was dissolved in CH2CI2 (i.e. DCM) (25ml, 5V), reserved. In a 50 ml glass reactor, was charged compound (III) (wherein R1 is ethyl, 3.5g, 0.7eq), triethylamine (4.29g, 1 .4eq) and CH2CI2 (25ml, 5V). the obtained solution was added dropwise to the DCM solution of compound of formula (X-a). After adding, the mixture was stirred for 7 h. Then water (50ml, 10V) was charged and the phase was separated. The organic layer was extracted with 2N aqueous HCI (20mlx2, 8V). The aqueous phase was adjusted to pH 8 with sodium bicarbonate. Then the obtained solution was extracted with DCM (25mlx2, 10V). The aqueous phase was concentrated under reduced pressure to obtain compound (II) (in which Ri is Ethyl) 2.17g, yield 41 .3%, GC purity 60%.

Reference： [1]Current Patent Assignee: HOLDING F.I.S. S.P.A. - WO2018/145860, 2018, A1 Location in patent: Paragraph 00152

73
[ 50-00-0 ]
[ 17136-36-6 ]
[ 84-65-1 ]
N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In 1,4-dioxane; benzene for 3h; Dean-Stark; Reflux;	1.1.2. 3'-Benzyl-10H-spiro[anthracene-9,5'-oxazolidin]-10-one (2b) A mixture of anthraquinone (624 mg, 3 mmol), N-benzylglycine (570 mg, 3.45 mmol), and paraformaldehyde (158 mg, 5.26 mmol of formaldehyde) was heated at reflux in mixture of dry benzene (15 mL) and dry 1,4-dioxane (7 mL) with magnetic stirring in a 50 mL round-bottom flask fitted with a Dean-Stark trap for 3 h. The resulting mixture was cooled to rt and the solid (if necessary) was filtered off. The residual solution was evaporated under reduced pressure to give the viscous oil, which solidified at room temperature.Yellow solid (1.02 g, quantitative yield), mp 118-120 °C (ref. 1).

Reference： [1]Buev, Evgeny M.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y. [Tetrahedron Letters, 2018, vol. 59, # 37, p. 3409 - 3412]

74
[ 1631-26-1 ]
[ 17136-36-6 ]
[ 67-64-1 ]
2,5-dibenzyl-4,4-dimethyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene at 130℃; for 18h;	1.1 Step 1. 2, 5-dibenzyl-4,4-dimethyltetrahydropyrrolo [3, 4-c] pyrrole-1, 3 (2H, 3aH) -dione The solution of 1-benzyl-1H-pyrrole-2,5-dione (23.4 g, 0.125 mol), 2- (benzylamino) acetic acid (31 g, 0.188 mol) and acetone (22 g, 0.375 mol) in touluene was stirred at 130 °C for 18 h. The precipicate after cooling to room temperature was filtered off and the filter cake was washed with EtOAc (50 mL). The filtrate was concentrated in vacuo and the crude product was purified by silica gel flash column chromatography (PE/EtOAc =5/1-3/2) to give the title compound (32.2 g, 74% yield).
	In toluene at 140℃; for 48h;	The first step Benzyl glycine 4a (7.06 g, 42.74 mmol), acetone (6.21 g, 106.85 mmol), 1-benzyl-2,5-dihydropyrrole-2,5-dione 4b (4.00 g, 21.37 mmol) and toluene (40 mL) were added into a 200 mL pot. The reaction mixture obtained was stirred at 140 °C for 48hrs. After completion of the reaction, the reaction mixture was concentrated, the crude product was purified by silica gel chromatography (PE/EtOAc = 100-0%) to give the compound 4c. 1H NMR (400 MHz, CDCl3) δ 7.40-7.32 (m, 10H), 4.77-4.72 (t, J = 5.2, 2H), 3.96-3.74 (m, 3H), 2.90-2.66 (m, 3H), 2.31 (s, 3H), 1.60 (s, 3H).

Reference： [1]Current Patent Assignee: JS INNOPHARM SHANGHAI - WO2019/76358, 2019, A1 Location in patent: Page/Page column 65
[2]Current Patent Assignee: CHINA RESOURCES NATIONAL CORPORATION - EP3656772, 2020, A1 Location in patent: Paragraph 0075; 0076; 0077

75
[ 17136-36-6 ]
[ 123-11-5 ]
[ 120329-58-0 ]
C₇₆H₁₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In chlorobenzene at 130℃; for 5h;	1 Example 1: Preparation method of N-benzyl-2-(4-methoxyphenyl)pyrrolidine [3',4',1,2][60]fullerene: Accurately weigh 36mg (0.05mmol) C60, 27 mg (0.20 mmol) of p-methoxybenzaldehyde and50 mg (0.30 mmol) of N-benzylglycine was added to a 100 mL thick-walled eggplant-shaped bottle. Then take 10 mL of chlorobenzene and shake it for 15 min. Dissolve C60 and aldehyde completely and mix glycine evenly. The oil bath is heated to a constant temperature of 130 ° C for 5 h. Heating was then stopped and the reactor was cooled to room temperature. The solvent is removed by rotary evaporation. The residual solid is sufficiently dissolved in a small amount of carbon disulfide and separated by column chromatography. Rinse with carbon disulfide and wash off the brown product strip. Rotating the solution by rotary evaporation gave a brownish black solid as a product. After drying under vacuum for 10 h, the yield was 67%.

Reference： [1]Current Patent Assignee: SOUTHWEST UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110066238, 2019, A Location in patent: Paragraph 0020; 0021; 0022

76
[ 17136-36-6 ]
[ 120329-58-0 ]
[ 100-10-7 ]
C₇₇H₂₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In chlorobenzene at 130℃; for 5h; Sonication;	1 Example 1:Preparation method of N-benzyl-2-(4-N,N-dimethylaminophenyl)pyrrolidine [3',4',1,2][60]fullerene: Accurately weigh 36mg (0.05mmol) C60,30 mg (0.20 mmol) of 4-N,N-dimethylaminobenzaldehyde and50 mg (0.30 mmol) of N-benzylglycine was added to100mL thick-walled eggplant-shaped bottle,Then take and add 10mL of chlorobenzene,Ultrasonic oscillation for 15 min,Allow C60 and aldehyde to dissolve completely and mix well with glycine,The oil bath is heated to a constant temperature of 130 ° C for 5 h.Heating was then stopped and the reactor was cooled to room temperature.The solvent is removed by rotary evaporation.The residual solid was sufficiently dissolved with a small amount of carbon disulfide, separated by column chromatography, washed with carbon disulfide, and the brown product strip was washed.Rotating the solution by rotary evaporation gave a brownish black solid as a product.After drying under vacuum for 10 h, the yield was 61%.

Reference： [1]Current Patent Assignee: SOUTHWEST UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110003087, 2019, A Location in patent: Paragraph 0026-0028

77
[ 17136-36-6 ]
C₁₀H₁₇NO₃ [ No CAS ]
C₁₈H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 130℃; for 16h;	The third step 5c (1.50 g, 7.53 mmol) and glycine 4a (2.49 g, 15.06 mmol) were dissolved in 20 mL toluene. The reaction mixture obtained was stirred at 130 °C for 16hrs. After completion of the reaction, water (10 mL) was added into the reaction mixture, then the mixture was extracted with EtOAc (15 mLx3), the organic phases were combined and wahsed with saturated brine (20 mLx1), dried over anhydrous sodium sulfate, filtered and concentrated, the crude product was purified by column chromatography (PE/EtOAc = 100-0%) to give 5d. 1H NMR (400 MHz, CDCl3) δ 7.38-7.34 (m, 2H), 7.30 (t, J = 8.0 Hz, 2H), 7.26-7.20 (m, 1H), 4.16 (d, J = 8.0 Hz, 2H), 3.97 (d, J = 4.0 Hz, 2H), 3.64-3.55 (m, 1H), 3.48-3.40 (m, 1H), 3.29 (d, J = 4.0 Hz, 1H), 3.11-2.98 (m, 2H), 2.84-2.73 (m, 1H), 2.45-2.36 (m, 1H), 1.87-1.93 (m, 1H), 1.30 (s, 6H), 1.25 (s, 3H).

Reference： [1]Current Patent Assignee: CHINA RESOURCES NATIONAL CORPORATION - EP3656772, 2020, A1 Location in patent: Paragraph 0096; 0100; 0101

78
[ 50-00-0 ]
[ 17136-36-6 ]
C₁₀H₁₄NO₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With hypophosphorous acid; acetic acid In water at 40℃; for 24h;

Reference： [1]Císařová, Ivana; Hermann, Petr; Kotek, Jan; Urbanovský, Peter [RSC Advances, 2020, vol. 10, # 36, p. 21329 - 21349]

79
[ 50-00-0 ]
[ 17136-36-6 ]
meso-tetrakis(pentafluorophenyl)-3-oxo-2-oxaporphyrin [ No CAS ]
C₅₂H₁₉F₂₀N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In toluene for 4h; Reflux; Inert atmosphere;	3.2.1. General Procedure for the Synthesis of Cycloadducts 3 General procedure: A solution of porpholactone 1 (50.0 mg, 0.05 mmol), N-substituted glycine (0.45 mmol), andparaformaldehyde (33.8 mg, 1.1 mmol) in toluene (25 mL) was heated at reflux under a nitrogenatmosphere for 4 h. Then, new portions of the N-substituted glycine (0.45 mmol) and paraformaldehyde(33.8 mg, 1.1 mmol) were added, and the mixture was refluxed for additional 4 h. The solvent wasevaporated, and the compounds were separated by preparative TLC using dichloromethane/hexane asthe eluent. The compound with higher Rf corresponded to unreacted porpholactone (~10%), and thefraction running immediately below it corresponded to the expected cycloadduct. Isolated yields: 3a =85%; 3b = 43%.

Reference： [1]Almeida Paz, Filipe A.; Cerqueira, Ana F. R.; Guieu, Samuel; Snarskis, Gustautas; Tomé, Augusto C.; Zurauskas, Jonas [Molecules, 2020, vol. 25, # 11]

80
[ 50-00-0 ]
[ 17136-36-6 ]
[ 2043-61-0 ]
1-((benzyl(methyl)amino)methyl)cyclohexane-1-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With benzoic acid In benzene for 3h; Dean-Stark; Reflux;	General procedure for the synthesis of Mannich bases 13a-d General procedure: Finely ground N-substituted glycine(3 mmol), paraformaldehyde (126 mg, 4.2 mmol of formaldehyde), benzoic acid (244 mg, 2 mmol),dry benzene (12 mL) and aldehyde (2 mmol) were sequentially added in 25 mL round-bottom flaskfitted with a Dean-Stark trap and equipped with a magnetic stirring bar. The mixture was refluxed for 3h, cooled to rt, and solid was filtered off if necessary. The resulting mixture was extracted with coldaqueous solution of HCl (3.4 mmol, 10 mL). Aqueous phase was washed with ether (7 mL), basifiedwith NaHCO3 to pH 8-9. Brine (10 mL) was added to the resulting solution, and it was extracted withether (3 × 10 mL). The combined organic layers were washed with brine, dried over Na2SO4, thesolvent was removed in vacuo at rt to give the desired Mannich bases 13a-d. The latter was purified bycolumn chromatography if necessary.

Reference： [1]Buev, Evgeny M.; Gorbunova, Evgeniya V.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y. [Synlett, 2020, vol. 31, # 4, p. 343 - 348]

81
[ 50-00-0 ]
[ 17136-36-6 ]
[ 78-84-2 ]
[ 96516-05-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With benzoic acid In benzene for 3h; Dean-Stark; Reflux;	General procedure for the synthesis of Mannich bases 13a-d General procedure: Finely ground N-substituted glycine(3 mmol), paraformaldehyde (126 mg, 4.2 mmol of formaldehyde), benzoic acid (244 mg, 2 mmol),dry benzene (12 mL) and aldehyde (2 mmol) were sequentially added in 25 mL round-bottom flaskfitted with a Dean-Stark trap and equipped with a magnetic stirring bar. The mixture was refluxed for 3h, cooled to rt, and solid was filtered off if necessary. The resulting mixture was extracted with coldaqueous solution of HCl (3.4 mmol, 10 mL). Aqueous phase was washed with ether (7 mL), basifiedwith NaHCO3 to pH 8-9. Brine (10 mL) was added to the resulting solution, and it was extracted withether (3 × 10 mL). The combined organic layers were washed with brine, dried over Na2SO4, thesolvent was removed in vacuo at rt to give the desired Mannich bases 13a-d. The latter was purified bycolumn chromatography if necessary.

Reference： [1]Buev, Evgeny M.; Gorbunova, Evgeniya V.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y. [Synlett, 2020, vol. 31, # 4, p. 343 - 348]

82
[ 17136-36-6 ]
2-(2-pyridine)-1,4-diphenyl-1,3-enyne [ No CAS ]
C₂₉H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 5,6-bis(5-methoxythiophen-2-yl)pyrazine-2,3-dicarbonitrile; caesium carbonate In tetrahydrofuran; 1,2-dichloro-ethane at 30℃; for 60h; Irradiation;

Reference： [1]Cao, Shanshan; Hu, Weigao; Jiang, Zhiyong; Zhan, Qiangqiang; Zhou, Hongwei [Chemical Science, 2021, vol. 12, # 19, p. 6543 - 6550]

83
ethyl but-3-en-2-yl(2-oxoethyl)carbamate [ No CAS ]
[ 17136-36-6 ]
rac-ethyl-(3aR,6aR)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In toluene at 110℃; for 16h;	Step (iv) rac-Ethyl-(3aR,6aR)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate To a stirred solution of ethyl but-3-en-2-yl-(2-oxoethyl)carbamate (4.7 g, 25.4 mmol) in toluene (100 mL) was added N-benzylglycine (CAS 17136-36-6, from Combi-blocks, 4.2 g, 25.4 mmol) at rt. The mixture was heated at 110 °C for 16 h then concentrated under reduced pressure. The residue was purified by column chromatography (basic aluminium oxide, 7% EtOAc in n-hexanes) to yield rac-ethyl (3aR,6aR)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (3.2 g, 11.1 mmol, 43% yield). LCMS: Method C, 1.33 min, two broad peaks merged, no baseline separation of the two diastereomers, MS: ES+ 289.3.

Reference： [1]Current Patent Assignee: MISSION THERAPEUTICS LIMITED - WO2021/249909, 2021, A1 Location in patent: Page/Page column 38-40

84
[ 17136-36-6 ]
ethyl (R)-but-3-en-2-yl(2-oxoethyl)carbamate [ No CAS ]
ethyl (3aR,4R,6aR)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate [ No CAS ]
ethyl (3aS,4R,6aS)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 % de	In toluene at 120℃; for 18h; Dean-Stark; Overall yield = 98 percent; Overall yield = 306 g;	Step (vii) Ethyl (3aR,4R,6aR)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate, mixture with ethyl (3aS,4R,6aS)-1-benzyl-4-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (~70 : 30 mixture of diastereomers) In a 10 L round-bottomed flask, equipped with Dean-Stark apparatus, a mixture of ethyl (R)-but-3-en- 2-yl-(2-oxoethyl)carbamate (200.0 g, 1079.7 mmol) in toluene (7.2 L, 36 vol) was stirred at rt. N-Benzylglycine (214.02 g, 1295.7 mmol) was added to the mixture, which was then heated at 120 °C for 18 h, allowed to cool to rt and concentrated under reduced pressure. The residue was poured in to saturated NaHCO3 solution (2000 mL) and was extracted with DCM (2 x 1000 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the subtitle compounds (~70 : 30 mixture of diastereomers) as a brown oil (306.0 g, 1061.06 mmol, 98% yield). LCMS: Method H3, 3.46 min, mixture of diastereomers, MS: ES+ 289.2; 1H NMR (400 MHz, CDCl3) δ ppm: 7.16 - 7.40 (m, 5H), 4.16 (m, 2H), 3.91 (m, 2H), 3.65 (m, 1H), 3.49 (m, 1H), 3.32 (m, 1H), 3.18 (m, 1H), 2.92 (m, 1H), 2.64 - 2.72 (m, 1H), 2.40 (s, 1H), 2.33 (m, 1H), 2.10 (m, 1H), 1.30 (t, 3H), 1.20 (d, J = 5.2 Hz, 3H); Chiral HPLC: Method Y26, 5.23 min - major peak; 5.61 min - minor peak. The method was repeated three times in an identical manner using ethyl (R)-but-3-en-2-yl-(2- oxoethyl)carbamate (515 g, 600 g and 760 g) to provide the subtitle compound (respectively 751 g, 880 g and 970 g). Combined weight of all four batches: 2907 g, 10.09 mol.

Reference： [1]Current Patent Assignee: MISSION THERAPEUTICS LIMITED - WO2021/249909, 2021, A1 Location in patent: Page/Page column 41; 44

85
[ 17136-36-6 ]
2-(1H-indol-5-yl)benzaldehyde [ No CAS ]
5-benzyl-1,4,5,6-tetrahydroindolo[4,5-d][2]benzazepine [ No CAS ]
N-benzyl-N-methyl-1,9-dihydroindeno[1,2-f]indole-9-amine [ No CAS ]
N-benzyl-N-methyl-1,4-dihydroindeno[1,2-e]indole-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 8% 3: 4%	In para-xylene for 2h; Reflux; regioselective reaction;	Reaction of Aldehydes 3a-d, 4, 5 with Amino Acids; General Procedure General procedure: A mixture of the corresponding aldehyde (1 mmol) and sarcosine, N-benzylglycine, pipecolinic acid, or 1,3-thiazolidine-4-carboxylic acid (each 3 mmol) in p-xylene (30 mL) was refluxed for 2 h. After cooling,the reaction mixture was filtered through a pad of Celite and concentrated. The crude product was purified by column chromatography on silica gel with MeOH-CH2Cl2 as eluent.

Reference： [1]Kovács, Ervin; Molnár, István G.; Mucsi, Zoltán; Nyerges, Miklós [Synthesis, 2022]

86
[ 17136-36-6 ]
2-(1-benzofuran-5-yl)benzaldehyde [ No CAS ]
5-benzyl-1,4,5,6-tetrahydrobenzofurano[4,5-d][2]benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In para-xylene for 2h; Reflux; regioselective reaction;	Reaction of Aldehydes 3a-d, 4, 5 with Amino Acids; General Procedure General procedure: A mixture of the corresponding aldehyde (1 mmol) and sarcosine, N-benzylglycine, pipecolinic acid, or 1,3-thiazolidine-4-carboxylic acid (each 3 mmol) in p-xylene (30 mL) was refluxed for 2 h. After cooling,the reaction mixture was filtered through a pad of Celite and concentrated. The crude product was purified by column chromatography on silica gel with MeOH-CH2Cl2 as eluent.

Reference： [1]Kovács, Ervin; Molnár, István G.; Mucsi, Zoltán; Nyerges, Miklós [Synthesis, 2022]

87
[ 17136-36-6 ]
2-(1-benzothiophen-5-yl)benzaldehyde [ No CAS ]
5-benzyl-1,4,5,6-tetrahydrobenzothiophen[4,5-d][2]benzazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In para-xylene for 2h; Reflux; regioselective reaction;	Reaction of Aldehydes 3a-d, 4, 5 with Amino Acids; General Procedure General procedure: A mixture of the corresponding aldehyde (1 mmol) and sarcosine, N-benzylglycine, pipecolinic acid, or 1,3-thiazolidine-4-carboxylic acid (each 3 mmol) in p-xylene (30 mL) was refluxed for 2 h. After cooling,the reaction mixture was filtered through a pad of Celite and concentrated. The crude product was purified by column chromatography on silica gel with MeOH-CH2Cl2 as eluent.

Reference： [1]Kovács, Ervin; Molnár, István G.; Mucsi, Zoltán; Nyerges, Miklós [Synthesis, 2022]

88
tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III) [ No CAS ]
[ 17136-36-6 ]
rac-[Ir(pq)₂(bgly)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methoxide In methanol at 65℃; for 12h; Darkness;

Reference： [1]Xiong, Ming-Feng; Ye, Bao-Hui [Organometallics, 2022, vol. 41, # 5, p. 617 - 626]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	17136-36-6	MDL No. :	MFCD00190772
Formula :	C₉H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KGSVNOLLROCJQM-UHFFFAOYSA-N
M.W :	165.19	Pubchem ID :	86965
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.6
TPSA :	49.33 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.29 cm/s

Log Po/w (iLOGP) :	1.34
Log Po/w (XLOGP3) :	-1.39
Log Po/w (WLOGP) :	0.71
Log Po/w (MLOGP) :	-1.11
Log Po/w (SILICOS-IT) :	1.1
Consensus Log Po/w :	0.13

[ CAS No. 17136-36-6 ] {[proInfo.proName]}

Quality Control of [ 17136-36-6 ]

Related Doc. of [ 17136-36-6 ]

Product Details of [ 17136-36-6 ]

Calculated chemistry of [ 17136-36-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 17136-36-6 ]

Application In Synthesis of [ 17136-36-6 ]

[ 17136-36-6 ] Synthesis Path-Upstream 1~5

[ 17136-36-6 ] Synthesis Path-Downstream 1~88

Pharmaceutical Intermediates of
[ 17136-36-6 ]

Sitafloxacin Related Intermediates

Related Functional Groups of
[ 17136-36-6 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-0.09
Solubility :	133.0 mg/ml ; 0.805 mol/l
Class :	Very soluble
Log S (Ali) :	0.86
Solubility :	1180.0 mg/ml ; 7.17 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.394 mg/ml ; 0.00238 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 17136-36-6 ] {[proInfo.proName]}

Quality Control of [ 17136-36-6 ]

Related Doc. of [ 17136-36-6 ]

Product Details of [ 17136-36-6 ]

Calculated chemistry of [ 17136-36-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 17136-36-6 ]

Application In Synthesis of [ 17136-36-6 ]

[ 17136-36-6 ] Synthesis Path-Upstream 1~5

[ 17136-36-6 ] Synthesis Path-Downstream 1~88

Pharmaceutical Intermediates of [ 17136-36-6 ]

Sitafloxacin Related Intermediates

Related Functional Groups of [ 17136-36-6 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 17136-36-6 ]

Related Functional Groups of
[ 17136-36-6 ]