Name: 2862-51-3|Cyclo(L-Phe-L-Phe)|99+%
Brand: Ambeed
SKU: A248251
Rating: 91 (32 reviews)

1
[ 3081-24-1 ]
[ 2862-51-3 ]

Reference： [1]Birkinshaw; Mohammed [Biochemical Journal, 1962, vol. 85, p. 523,525]
[2]Vejdelek [Collection of Czechoslovak Chemical Communications, 1950, vol. 15, p. 929,931]

2
[ 63-91-2 ]
[ 374674-82-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	In ethylene glycol for 24h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Marcuccio, Sebastian M.; Elix, John A. [Australian Journal of Chemistry, 1984, vol. 37, # 11, p. 2397 - 2402]

3
[ 13734-34-4 ]
[ 7524-50-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Grina, Jonas A.; Stermitz, Frank R. [Tetrahedron Letters, 1981, vol. 22, # 52, p. 5257 - 5258]

4
[ 4892-10-8 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With hydrogen bromide; acetic acid In methanol for 12h; Ambient temperature;
	With hydrogen bromide; sodium hydrogencarbonate; acetic acid 1.)30 min, R_.T_., 2.)1-butanol, 2 d, reflux; Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: 73 percent / formic acid, Pd black / methanol / 4 h / 20 °C 2: 15 percent / triethylamine / ethanol / 2 h / Heating

Reference： [1]Ishibashi, Norio; Kouge, Katsushige; Shinoda,Ichizo; Kanehisa, Hidenori; Okai, Hideo [Agricultural and Biological Chemistry, 1988, vol. 52, # 3, p. 819 - 828]
[2]Egusa, Syun; Takagi, Jun; Sisido, Masahiko; Imanishi, Yukio [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2195 - 2202]
[3]Kotlova, E. K.; Levin, E. D.; Yusupova, M. P.; Rozynov, B. V.; Stepanov, V. M. [Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 11, p. 678 - 686][Bioorganicheskaya Khimiya, 1994, vol. 20, # 11, p. 1186 - 1195]

5
[ 150582-52-8 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With methanol r.t., 24 h, then reflux, 1 h;

Reference： [1]Burger, K.; Rudolph, M.; Windeisen, E.; Worku, A.; Fehn, S. [Monatshefte fur Chemie, 1993, vol. 124, # 4, p. 453 - 464]

6
[ 2862-51-3 ]
[ 74-88-4 ]
[ 61125-52-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In N,N-dimethyl-formamide
77%	With sodium hydride In N,N-dimethyl-formamide
45%	With sodium hydride In N,N-dimethyl-formamide 1.) 50 deg C, 3 h, 2.) room temperature, 24 h;

Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;

Reference： [1]Donkor; Sanders, M. Lee [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2647 - 2649]
[2]Grina, Jonas A.; Stermitz, Frank R. [Tetrahedron Letters, 1981, vol. 22, # 52, p. 5257 - 5258]
[3]Radding, W.; Donzel, B.; Ueyama, N.; Goodman, M. [Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 5999 - 6005]
[4]Zeng, Yibin; Li, Qingshan; Hanzlik, Robert P.; Aube, Jeffrey [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 3034 - 3038]

7
[ 2862-51-3 ]
[ 79982-83-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With borane-THF In tetrahydrofuran at 0℃; Reflux; Stage #2: With methanol; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 12h;	19 (2S,5S)-2,5-Bis(phenylmethyl)piperazine 21 To a vigorously stirred suspension of (3S,6S)-3,6-bis(phenylmethyl)- piperazine-2,5-dione (4.30 g, 14.60 mmol) in THF (72 mL), BH3 FontWeight="Bold" FontSize="10" THF (1 M solution in THF, 87 mL, 84 mmol) was added dropwise at 0°C. The mixture was stirred for 1 h, warming to r.t and heated to reflux for 2 h The solution was filtered, cooled at 0°C, carefully quenched with methanol (20 mL), and then concentrated under reduced pressure. The residual crystalline material was dissolved in methanol (17 mL) and THF (7 mL), and then a suspension of 10% palladium on carbon (177 mg, 50% wet) in methanol (17 mL) was added. The mixture was stirred for 12 h at r t. The crude reaction mixture was filtered and concentrated under reduce pressure. Purification by flash column chromatography (8:92 methanoLchloroform) gave 21 as colourless oil (3.20 g, 82%); Rf 0.51 (5:95 methanol:chloroform); IR (v, neat/cm"1): 3320, 3020, 2700, 1455, 1305 1 190, 990, 742; H NMR (500 MHz, CDCI3) δ: 1 .59 (br s, 2H, NH), ), 2.79-3.03 (overlap m, 10H, ArCH2, NHCH2, NHCH), 7.21 -7.35 (m, 10H, ArH); 3C NMR (125.8 MHz, CDCI3) δ: 38.1 (2 ArCH2), 47.5 (2 NHCH2), 55.2 (2 NHCH), 125.7 (2 CH) 128.0 (4 x CH), 128.7 (4 x CH), 138.9 (2 χ C); HRMS (Fl)+: m/z calcd for C18H22N2 [M+ 266.1775, found 266.1783.
78%	With sodium tetrahydroborate In 1,2-dimethoxyethane at 0℃; for 48h; Heating;
75%	With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere;	5.2.1. General procedures for the synthesis of 1,4-piperazines General procedure: All 1,4-piperazine (1-5a-c) were prepared from the corresponding cyclic dipeptides (CDPs). The latter were prepared by solid-phase peptide synthesis with oxime resin using the appropriate phenylalanine or tyrosine derivatives. 31,32 1,4-Piperazines were readily produced by the reduction of CDPs using LiAlH4 (1 M in THF) for 48 h in dry THF under an inert atmosphere. Once the reaction was completed, Na2SO410H2O was added to neutralize residual LiAlH4 and other active species, and the mixture was refluxed for 30 min. 37,38 Residual solids were eliminated by filtration which led to the desired crude aromatic 1,4-piperazines with 80% to 87% yields. Crude products were purified by flash chromatography using CH2Cl2/MeOH as eluent.

35%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;
	With sodium tetrahydroborate; titanium tetrachloride
	With borane In tetrahydrofuran for 4h; Heating;
	With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Reflux;
	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Reflux;	4.3. Reduction of 2,5-diketopiperazines General procedure: 4.3.1. General procedure. The 2,5-diketopiperazine was partially dissolved in anhydrous THF in an oven-dried three-neck flask under argon. The solution was cooled to 0 °C and LiAlH4 (1.0 M THF, 12 equiv) was added dropwise. The mixture was allowed to warm at room temperature and the reaction was refluxed overnight. The mixture was then cooled to 0 °C and treated with Na2SO4 decahydrate. The suspension obtained was refluxed for 30 min and then filtered. The solvent was evaporated under reduced pressure and the crude product was dried under vacuum and used as in the next step.

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2 Location in patent: Page/Page column 38
[2]Soai, Kenso; Hayashi, Hiroshi; Hasegawa, Hitoshi [Heterocycles, 1986, vol. 24, # 5, p. 1287 - 1289]
[3]Simon, Gaëlle; Bérubé, Christopher; Paquet-Côté, Pierre-Alexandre; Grenier, Daniel; Voyer, Normand [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 23]
[4]Selvakumar, Sermadurai; Sivasankaran, Dhanasekaran; Singh, Vinod K. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 15, p. 3156 - 3162]
[5]Soai, Kenso; Hayashi, Hiroshi; Shinozaki, Akihiro; Umebayashi, Hideaki; Yamada, Yasuyuki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 9, p. 3450 - 3452]
[6]Jung, Michael E.; Rohloff, John C. [Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4909 - 4913]
[7]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]
[8]Bérubé, Christopher; Cardinal, Sébastien; Boudreault, Pierre-Luc; Barbeau, Xavier; Delcey, Nicolas; Giguère, Martin; Gleeton, Dave; Voyer, Normand [Tetrahedron, 2015, vol. 71, # 42, p. 8077 - 8084]

8
[ 2862-51-3 ]
D,L-3,6-diphenylpiperazine-2,5-diphenylpiperazine-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium isopropylate In isopropyl alcohol for 0.5h; Heating;

Reference： [1]Kricheldorf, Hans R. [Organic Magnetic Resonance, 1980, vol. 13, # 1, p. 52 - 58]

9
[ 2862-51-3 ]
2-benzyl-5-benzoylpiperazine-3,6-dione [ No CAS ]
2,5-dibenzoylpiperazine-3,6-diones [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water; iron(III) chloride; acetone for 4h; Irradiation; Yield given. Yields of byproduct given;
	With water; iron(III) chloride; acetone Irradiation; Yield given. Yields of byproduct given;

Reference： [1]Barbier, Michel [Heterocycles, 1985, vol. 23, # 2, p. 345 - 348]
[2]Barbier, Michel [Heterocycles, 1985, vol. 23, # 2, p. 345 - 348]

10
L-phenylalanyl-L-phenylalanine methyl ester [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
15%	With triethylamine In ethanol for 2h; Heating;
	With iso-butanol In toluene at 20℃;
396 mg	In toluene; iso-butanol at 90℃; for 4h;

Reference： [1]Kotlova, E. K.; Levin, E. D.; Yusupova, M. P.; Rozynov, B. V.; Stepanov, V. M. [Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 11, p. 678 - 686][Bioorganicheskaya Khimiya, 1994, vol. 20, # 11, p. 1186 - 1195]
[2]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]
[3]Rajput, Sunnia; McLean, Kirsty J.; Poddar, Harshwardhan; Selvam, Irwin R.; Nagalingam, Gayathri; Triccas, James A.; Levy, Colin W.; Munro, Andrew W.; Hutton, Craig A. [Journal of Medicinal Chemistry, 2019, vol. 62, # 21, p. 9792 - 9805]

Yield	Reaction Conditions	Operation in experiment
	Z-Phe-Phe-OMe, N-Methyl-morpholin, H2/Pd/C;

12
[ 13122-89-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate With formic acid at 20℃; for 2h; Stage #2: In toluene; iso-butanol for 2h; Reflux;	15 (3S,6S)-3,6- Bis(phenylmethyl)piperazine-2,5-dione, 17 A solution of (S)-methyl 2-((S)-2-(fe/?-butoxycarbonylamino)-3-phenyl- propanamido)-3- phenylpropanoate (6.80 g, 15.9 mmol) in formic acid (159 ml_) was stirred for 2 h at r.t and the solution was concentrated under reduced pressure. The residue was dissolved in sec-butanol (600 ml_) and toluene (160 ml_) and refluxed for 2 h. The resulting precipitate was filtered, and then recrystallised from methanol/acteone to give 17 as white solid (4.30 g, 92%); IR (v, KBr/cm" ): 3187, 3080, 1669, 1665, 1497, 1461 ; H NMR (500 MHz, CF3C02D) δ: 2.32 (dd, J = 14.0, 7.6 Hz, 2H, Η ), 3.08 (dd, J = 14.0, 3.7 Hz, 2H, H2), 4.58 (dd, J = 7.0, 4.0 Hz, 2H, NHCH), 7.13 (d, J = 7.5 Hz, 4H, ArH), 7.34-7.42 (m, 6H, ArH); 3C NMR (125.8 MHz, CF3C02D) δ: 39.6 (2 ArCH2), 56.6 (2 NHCH), 128.5 (2 CH), 129.4 (4 CH), 129.9 (4 χ CH), 133.6 (2 χ C), 170.9 (2 χ NHCO); mp 308- 310 °C; [a]22D -99.0 (c 0.2, AcOH); HRMS (Fl)+: m/z calcd for C18H18N202 [M+ 294.1368, found 294.1355.
90%	Stage #1: (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate With formic acid; methoxybenzene at 20℃; for 3h; Stage #2: In toluene; iso-butanol for 3h; Heating; Further stages.;
87%	Stage #1: (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate With formic acid Stage #2: With iso-butanol In toluene Heating;

80%	Stage #1: (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate With formic acid at 20℃; for 1h; Stage #2: In toluene; butan-1-ol for 1.5h; Heating; Further stages.;
	With formic acid at 20℃; for 2h;
	Multi-step reaction with 2 steps 1: formic acid / 2 h / 20 °C 2: iso-butanol / toluene / 20 °C
	Multi-step reaction with 2 steps 1: formic acid / 20 °C 2: iso-butanol; toluene / 4 h / 90 °C

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2 Location in patent: Page/Page column 36-37
[2]Joshi; Verma, Sandeep [Tetrahedron Letters, 2008, vol. 49, # 27, p. 4231 - 4234]
[3]Donkor; Sanders, M. Lee [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2647 - 2649]
[4]Pichowicz, Mark; Simpkins, Nigel S.; Blake, Alexander J.; Wilson, Claire [Tetrahedron, 2008, vol. 64, # 17, p. 3713 - 3735]
[5]Jeedigunta, Shanti; Krenisky, Joann M.; Kerr, Russell G. [Tetrahedron, 2000, vol. 56, # 21, p. 3303 - 3307]
[6]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]
[7]Rajput, Sunnia; McLean, Kirsty J.; Poddar, Harshwardhan; Selvam, Irwin R.; Nagalingam, Gayathri; Triccas, James A.; Levy, Colin W.; Munro, Andrew W.; Hutton, Craig A. [Journal of Medicinal Chemistry, 2019, vol. 62, # 21, p. 9792 - 9805]

13
[ 63-91-2 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethylene glycol at 195℃; for 18h; Inert atmosphere;
	In water at 220℃;
	Multi-step reaction with 3 steps 1: 95 percent / 1 M HCl / 1 h / Heating 2: 40 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride, 1-hydroxybenzotriazole / CH₂Cl₂; triethylamine 3: 1.)HBr, acetic acid 2.)NaHCO₃ / 1.)30 min, R_.T_., 2.)1-butanol, 2 d, reflux

	Multi-step reaction with 3 steps 1: 71 percent / 1 M NaOH / H₂O 2: 40 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride, 1-hydroxybenzotriazole / CH₂Cl₂; triethylamine 3: 1.)HBr, acetic acid 2.)NaHCO₃ / 1.)30 min, R_.T_., 2.)1-butanol, 2 d, reflux
	With phosphorus trichloride In tetrahydrofuran for 2h; Reflux;

Reference： [1]Manchineella, Shivaprasad; Voshavar, Chandrashekhar; Govindaraju, Thimmaiah [European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4363 - 4369]
[2]Togashi, Takanari; Umetsu, Mitsuo; Tsuchizaki, Hiroyuki; Ohara, Satoshi; Naka, Takashi; Adschiri, Tadafumi [Chemistry Letters, 2006, vol. 35, # 6, p. 636 - 637]
[3]Egusa, Syun; Takagi, Jun; Sisido, Masahiko; Imanishi, Yukio [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2195 - 2202]
[4]Egusa, Syun; Takagi, Jun; Sisido, Masahiko; Imanishi, Yukio [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2195 - 2202]
[5]Location in patent: experimental part Guo, Yanchun; Cao, Shuxia; Wei, Donghui; Zong, Xiangkun; Yuan, Xingbo; Tang, Mingsheng; Zhao, Yufen [Journal of Mass Spectrometry, 2009, vol. 44, # 8, p. 1188 - 1194]

14
[ 13734-34-4 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 60 percent / EDC; Et₃N / CH₂Cl₂ 2.1: 96 percent formic acid 2.2: 87 percent / sec-butanol / toluene / Heating

Reference： [1]Donkor; Sanders, M. Lee [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2647 - 2649]

15
[ 7524-50-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 60 percent / EDC; Et₃N / CH₂Cl₂ 2.1: 96 percent formic acid 2.2: 87 percent / sec-butanol / toluene / Heating

Reference： [1]Donkor; Sanders, M. Lee [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2647 - 2649]

16
[ 13734-34-4 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DCC; Et₃N / dimethylformamide; acetonitrile / 14 h / 0 °C 2: formic acid / 2 h / 20 °C

Reference： [1]Jeedigunta, Shanti; Krenisky, Joann M.; Kerr, Russell G. [Tetrahedron, 2000, vol. 56, # 21, p. 3303 - 3307]

17
[ 7524-50-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DCC; Et₃N / dimethylformamide; acetonitrile / 14 h / 0 °C 2: formic acid / 2 h / 20 °C

Reference： [1]Jeedigunta, Shanti; Krenisky, Joann M.; Kerr, Russell G. [Tetrahedron, 2000, vol. 56, # 21, p. 3303 - 3307]

18
[ 2577-90-4 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,2,4-Triazole; 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 24h;
	Multi-step reaction with 3 steps 1: 85 percent / acetonitrile; H₂O / 24 h / thermolysin 2: 73 percent / formic acid, Pd black / methanol / 4 h / 20 °C 3: 15 percent / triethylamine / ethanol / 2 h / Heating

Reference： [1]Yang, Xing; Birman, Vladimir B. [Organic Letters, 2009, vol. 11, # 7, p. 1499 - 1502]
[2]Kotlova, E. K.; Levin, E. D.; Yusupova, M. P.; Rozynov, B. V.; Stepanov, V. M. [Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 11, p. 678 - 686][Bioorganicheskaya Khimiya, 1994, vol. 20, # 11, p. 1186 - 1195]

19
[ 1161-13-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / acetonitrile; H₂O / 24 h / thermolysin 2: 73 percent / formic acid, Pd black / methanol / 4 h / 20 °C 3: 15 percent / triethylamine / ethanol / 2 h / Heating

Reference： [1]Kotlova, E. K.; Levin, E. D.; Yusupova, M. P.; Rozynov, B. V.; Stepanov, V. M. [Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 11, p. 678 - 686][Bioorganicheskaya Khimiya, 1994, vol. 20, # 11, p. 1186 - 1195]

20
[ 1161-13-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 40 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride, 1-hydroxybenzotriazole / CH₂Cl₂; triethylamine 2: 1.)HBr, acetic acid 2.)NaHCO₃ / 1.)30 min, R_.T_., 2.)1-butanol, 2 d, reflux

Reference： [1]Egusa, Syun; Takagi, Jun; Sisido, Masahiko; Imanishi, Yukio [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2195 - 2202]

21
[ 7524-50-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 40 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride, 1-hydroxybenzotriazole / CH₂Cl₂; triethylamine 2: 1.)HBr, acetic acid 2.)NaHCO₃ / 1.)30 min, R_.T_., 2.)1-butanol, 2 d, reflux
	Multi-step reaction with 3 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / -5 - 0 °C 2: formic acid / 2 h / 20 °C 3: iso-butanol / toluene / 20 °C
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2.1: formic acid / 2 h / 20 °C 2.2: 2 h / Reflux

Reference： [1]Egusa, Syun; Takagi, Jun; Sisido, Masahiko; Imanishi, Yukio [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2195 - 2202]
[2]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]
[3]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2

22
[ 2862-51-3 ]
[ 114409-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium borohydride-titanium tetrachloride 2: 62 percent / triethylamine / CH₂Cl₂ / 13 h

Reference： [1]Soai, Kenso; Hayashi, Hiroshi; Shinozaki, Akihiro; Umebayashi, Hideaki; Yamada, Yasuyuki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 9, p. 3450 - 3452]

23
[ 2862-51-3 ]
[ 114409-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium borohydride-titanium tetrachloride 2: 82 percent / triethylamine / CH₂Cl₂ / 13 h

Reference： [1]Soai, Kenso; Hayashi, Hiroshi; Shinozaki, Akihiro; Umebayashi, Hideaki; Yamada, Yasuyuki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 9, p. 3450 - 3452]

24
[ 2862-51-3 ]
[ 114409-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium borohydride-titanium tetrachloride 2: 82 percent / triethylamine / CH₂Cl₂ / 13 h 3: 1.) LDA; 2.) HMPA / 1.) THF, -30 deg C, 30 min; 2.) -78 deg C, 3 h

Reference： [1]Soai, Kenso; Hayashi, Hiroshi; Shinozaki, Akihiro; Umebayashi, Hideaki; Yamada, Yasuyuki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 9, p. 3450 - 3452]

25
[ 2862-51-3 ]
(R)-1-[(2S,5S)-2,5-Dibenzyl-4-((R)-2-methyl-3-phenyl-propionyl)-piperazin-1-yl]-2-methyl-3-phenyl-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium borohydride-titanium tetrachloride 2: 62 percent / triethylamine / CH₂Cl₂ / 13 h 3: 1.) LDA / 1.) THF, -30 deg C, 30 min; 2.) -78 deg C, 3 h

Reference： [1]Soai, Kenso; Hayashi, Hiroshi; Shinozaki, Akihiro; Umebayashi, Hideaki; Yamada, Yasuyuki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 9, p. 3450 - 3452]

26
[ 824-94-2 ]
[ 2862-51-3 ]
[ 1024013-09-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 0℃; for 4h; Further stages.;

Reference： [1]Pichowicz, Mark; Simpkins, Nigel S.; Blake, Alexander J.; Wilson, Claire [Tetrahedron, 2008, vol. 64, # 17, p. 3713 - 3735]

27
[Ru(η(6)-cymene)(acetone)3](CF3SO3)2 [ No CAS ]
[ 2862-51-3 ]
[(Ru(η(6)-cymene))2(η(6)-(C6H5CH2CHCONH))2](CF3SO3)4 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In dichloromethane Ar-atmosphere; refluxing Ru-complex with 0.5 equiv. of ligand for 24 h (pptn.); collection, washing (CH2Cl2, Et2O), drying (vac.); elem. anal.;

Reference： [1]Wolff; Sheldrick [Journal of Organometallic Chemistry, 1997, vol. 531, # 1-2, p. 141 - 149]

28
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-methionyl)-L-cysteinyl]LHDI[S-(L-methionyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LHDI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
cyclo(-Phe-Met-) [ No CAS ]
[ 69744-12-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 8% 2: 42% 3: 35%	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid for 4h; aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

29
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LAAI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl-L-phenylalanyl)-L-cysteinyl]LAAICRELARIRRLLGER-CONH₂ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

30
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LDDI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl-L-phenylalanyl)-L-cysteinyl]LDDICRELARIRRLLGER-CONH₂ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

31
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LDHI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILSCLDHI[S-(L-phenylalanyl-L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

32
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LHDI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl-L-phenylalanyl)-L-cysteinyl]LHDICRELARIRRLLGER-CONH₂ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 35% 2: 31%	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid for 4h; aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

33
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl)-L-cysteinyl]LHHI[S-(L-phenylalanyl)-L-cysteinyl]RELARIRRLLGER-CONH₂ [ No CAS ]
[N-(p-acetamidobenzoyl)-R]LENILS[S-(L-phenylalanyl-L-phenylalanyl)-L-cysteinyl]LHHICRELARIRRLLGER-CONH₂ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

34
[ 1021171-70-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-morpholineethanesulfonic acid; tris(2-carboxyethyl)phosphine; [N-(p-acetamidobenzoyl)R]LENILS[S-(acetamidomethyl)-L-cysteinyl]LHHICRELARIRRLLGER-CONH₂

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

35
[ 1021171-56-1 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2-carboxyethyl)phosphine; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid aq. buffer;

Reference： [1]Huang, Zheng-Zheng; Leman, Luke J.; Ghadiri, M. Reza [Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1758 - 1761]

36
tert-butyl (tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalaninate [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	In water at 250℃; for 0.166667h; Microwave irradiation;

Reference： [1]Location in patent: experimental part Perez-Picaso, Lemuel; Escalante, Jaime; Olivo, Horacio F.; Rios, Maria Yolanda [Molecules, 2009, vol. 14, # 8, p. 2836 - 2849]

37
L-Leu-O-Bzl [ No CAS ]
[ 3081-24-1 ]
(3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

38
D-Leu-O-Bzl [ No CAS ]
[ 3081-24-1 ]
[ 189502-13-4 ]
[ 952-43-2 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

39
L-Tyr-O-Bzl [ No CAS ]
[ 3081-24-1 ]
[ 2862-51-3 ]
(3S,6S)-3-benzyl-6-(4-hydroxybenzyl)piperazine-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

40
D-Tyr-O-Bzl [ No CAS ]
[ 3081-24-1 ]
[ 1215092-11-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

41
D-Phe-O-Bzl [ No CAS ]
[ 3081-24-1 ]
[ 374674-82-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

42
D-Val-O-Bzl [ No CAS ]
[ 3081-24-1 ]
(3S,6R)-3-benzyl-6-isopropyl-2,5-piperazinedione [ No CAS ]
[ 15099-55-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 12h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

43
[ 54594-06-8 ]
[ 3081-24-1 ]
[ 1215092-08-2 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

44
[ 16338-48-0 ]
[ 3081-24-1 ]
[ 1215092-09-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

45
[ 61-90-5 ]
[ 3081-24-1 ]
[ 3303-55-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

46
[ 63-68-3 ]
[ 3081-24-1 ]
[ 15080-84-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

47
[ 63-91-2 ]
[ 3081-24-1 ]
[ 2577-40-4 ]
[ 2862-51-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 580 - 582
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

48
[ 2577-90-4 ]
[ 2577-40-4 ]
[ 2578-81-6 ]
[ 17528-17-5 ]
[ 2862-51-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 580 - 582

49
[ 3081-24-1 ]
[ 103676-11-5 ]
[ 2577-40-4 ]
[ 2578-81-6 ]
[ 2862-51-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 580 - 582

50
[ 3081-24-1 ]
[ 23235-01-0 ]
[ 1215092-10-6 ]
[ 2862-51-3 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 580 - 582

51
[ 3081-24-1 ]
[ 73-22-3 ]
[ 24587-41-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-S In dimethyl sulfoxide at 50℃; for 15h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Usuki, Hirokazu; Uesugi, Yoshiko; Arima, Jiro; Yamamoto, Yukihiro; Iwabuchi, Masaki; Hatanaka, Tadashi [Chemical Communications, 2010, vol. 46, # 4, p. 580 - 582]

52
N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide [ No CAS ]
[ 2862-51-3 ]
[ 95713-60-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With hydrogenchloride; water at 110℃; Stage #2: N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide With triethylamine In water; acetone at 40℃; for 1h;

Reference： [1]Location in patent: experimental part Wang, Jia-Ming; Ding, Guang-Zhi; Fang, Lei; Dai, Jun-Gui; Yu, Shi-Shan; Wang, Ying-Hong; Chen, Xiao-Guang; Ma, Shuang-Gang; Qu, Jing; Xu, Song; Du, Dan [Journal of Natural Products, 2010, vol. 73, # 7, p. 1240 - 1249]

53
[ 338-69-2 ]
[ 2577-90-4 ]
[ 3918-88-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

54
[ 54594-06-8 ]
[ 2577-90-4 ]
[ 1215092-08-2 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

55
[ 16338-48-0 ]
[ 2577-90-4 ]
[ 1215092-09-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

56
[ 632-20-2 ]
[ 2577-90-4 ]
L-Phe-D-Thr-OH [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

57
[ 328-38-1 ]
[ 2577-90-4 ]
L-Phe-D-Leu-OH [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

58
[ 61-90-5 ]
[ 2577-90-4 ]
[ 3303-55-7 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

59
[ 73-32-5 ]
[ 2577-90-4 ]
[ 22951-94-6 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

60
[ 63-68-3 ]
[ 2577-90-4 ]
[ 15080-84-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

61
[ 63-91-2 ]
[ 2577-90-4 ]
[ 2577-40-4 ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

62
[ 556-02-5 ]
[ 2577-90-4 ]
[ 66421-18-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

63
[ 2577-90-4 ]
[ 17528-16-4 ]
[ 2577-40-4 ]
[ 2578-81-6 ]
[ 17528-17-5 ]
methyl ester of pentaphenylalanine [ No CAS ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

64
[ 2577-90-4 ]
[ 673-06-3 ]
L-phenylalanyl-D-phenylalanine [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

65
[ 2577-90-4 ]
[ 60-18-4 ]
[ 17355-18-9 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

66
[ 2577-90-4 ]
[ 23235-01-0 ]
[ 1215092-10-6 ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

67
[ 2577-90-4 ]
[ 73-22-3 ]
[ 24587-41-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

68
[ 2577-90-4 ]
[ 153-94-6 ]
[ 66421-20-3 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

69
[ 2577-90-4 ]
[ 58-60-6 ]
[ 5001-55-8 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aminolysin-A In water; dimethyl sulfoxide at 50℃; for 6h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Usuki, Hirokazu; Yamamoto, Yukihiro; Arima, Jiro; Iwabuchi, Masaki; Miyoshi, Shozo; Nitoda, Teruhiko; Hatanaka, Tadashi [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2327 - 2335]

70
[ 2360-97-6 ]
[ 2577-40-4 ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

71
[ 3081-24-1 ]
[ 103676-11-5 ]
[ 1078737-21-9 ]
[ 1296838-21-5 ]
[ 2577-40-4 ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2327 - 2335

72
Fmoc-L-Phe-L-Phe-OMe [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With piperidine In dichloromethane	1 Synthesis of cyclic Phenylalanylphenylalanine [(3S,65)-3,6-dibenzylpiperazine-2,5- dione (CDP 1) or cyclic (Phe-Phe)] It is achieved through a robust and straight forward synthetic route developed as shown in Scheme 1. 9-Fluorenylmethyloxycarbonyl (Fmoc)- protected phenylalanine (Fmoc-Phe- OH) was condensed with phenylalanine methylester (H-Phe-OMe) using standard peptide coupling reagents to give the protected dipeptide Fmoc-Phe-Phe-OMe. The Fmoc-Phe- Phe-OMe is subjected to Fmoc-deprotection with 10% piperdine in dichloromethane. During this deprotection process the dipeptide methylester undergo cyclization to give Cyclic Dipeptide in quantitative yield.

Reference： [1]Current Patent Assignee: JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH - WO2011/55247, 2011, A1 Location in patent: Page/Page column 16-17

73
[ 302-72-7 ]
phenylalanine ethyl phosphate [ No CAS ]
[ 2577-40-4 ]
[ 2578-81-6 ]
[ 2667-02-9 ]
[ 2862-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5645 - 5647

74
[ 3182-95-4 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In 1,4-dioxane at 135℃; for 19h; Inert atmosphere;

Reference： [1]Gnanaprakasam, Boopathy; Balaraman, Ekambaram; Ben-David, Yehoshoa; Milstein, David [Angewandte Chemie - International Edition, 2011, vol. 50, # 51, p. 12240 - 12244]

75
[ 3182-95-4 ]
[ 100-46-9 ]
[ 6455-20-5 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 58% 2: 35%	With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene for 6h; Inert atmosphere; Reflux;

Reference： [1]Gnanaprakasam, Boopathy; Balaraman, Ekambaram; Ben-David, Yehoshoa; Milstein, David [Angewandte Chemie - International Edition, 2011, vol. 50, # 51, p. 12240 - 12244]

76
[ 106-95-6 ]
[ 2862-51-3 ]
[ 1361412-90-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 15h; Inert atmosphere;

Reference： [1]Nicolaou; Giguere, Denis; Totokotsopoulos, Sotirios; Sun, Ya-Ping [Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 728 - 732]

77
[ 2862-51-3 ]
C₂₄H₂₄N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 1.2: 15 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hexamethyldisilazane; sulfur / tetrahydrofuran; toluene / 0.55 h / 25 °C / Inert atmosphere 2.2: 0.77 h / 0 - 25 °C / Inert atmosphere 2.3: 0.17 h

Reference： [1]Nicolaou; Giguere, Denis; Totokotsopoulos, Sotirios; Sun, Ya-Ping [Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 728 - 732]

78
[ 2862-51-3 ]
C₂₆H₃₀N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 1.2: 15 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hexamethyldisilazane; sulfur / tetrahydrofuran; toluene / 0.55 h / 25 °C / Inert atmosphere 2.2: 0.77 h / 0 - 25 °C / Inert atmosphere 2.3: 15 h / 0 - 25 °C / Inert atmosphere

Reference： [1]Nicolaou; Giguere, Denis; Totokotsopoulos, Sotirios; Sun, Ya-Ping [Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 728 - 732]

79
[ 2862-51-3 ]
1,2,5-tribenzylpiperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C

Reference： [1]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]

80
[ 13734-34-4 ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Stage #2: With trifluoroacetic acid In dichloromethane for 0.5h; Stage #3: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine Further stages;	6 4.2.1. General procedure General procedure: 4.2.1.1. Coupling of the first Boc protected α-amino acid on oxime resin. A desired quantity of oxime resin (1.12 mmol/g) was added to a peptide synthesis vessel. The resin was treated three times with CH2Cl2. Amino acid (3.0 equiv) and HOBt (3.0 equiv) were dissolved in DMF in a 100 mL flask and the mixture was stirred for few minutes at 0 °C. DIC (3.0 equiv), DIEA (3.0 equiv) and DMAP (0.1 equiv) were introduced into the peptide synthesis vessel and the mixture was stirred mechanically for 3 h. The mixture was filtered under vacuum and the resin was washed [DMF (3x100 mL), MeOH (3x100 mL), DMF (3x100 mL), MeOH (3x100 mL)] and dried under reduced pressure. 4.2.1.3. Removal of the Boc protecting group. The resin was treated three times with CH2Cl2 (100 mL). A 50% v/v solution of trifluoroacetic acid (TFA) in CH2Cl2 was added to the peptide synthesis vessel, which was stirred for 30 min. Then, the mixture was filtered under vacuum and the resin was washed with DMF (3x100 mL), MeOH (3x100 mL), DMF (3x100 mL), MeOH(3x100 mL) and with a solution of 10% v/v DIEA in CH2Cl2 (100 mL). 4.2.1.4. Coupling of the second Boc protected α-amino acid. The amino acid (3.0 equiv) was dissolved in DMF in a 100 mL flask. The solution was cooled to 0 °C, then HBTU (3.0 equiv) and HOBt (3.0 equiv) were added. The mixture was poured into the peptide synthesis vessel in which the resin has been previously treated with CH2Cl2. DIEA (6.0 equiv) was also added to the vessel and the mixture was stirred for 3 h. After filtration under vacuum, the resin was washed [DMF (3x100 mL), MeOH (3x100 mL), DMF (3x100 mL) and MeOH (3x100 mL)] and dried reduced under pressure. The Kaiser nihydrin test was performed to monitor the efficiency of the coupling, and the coupling procedure was repeated if needed. 4.2.1.5. Cyclization/cleavage from the resin. First, the Boc group was removed using procedure described in (4.2.1.3), but without the 10% v/v DIEA/CH2Cl2 washing step. After drying, CH2Cl2 and DIEA (2.5 equiv) were added to the peptide synthesis vessel and the mixture was stirred for 2 min. Acetic acid (5.0 equiv) was then added and the content was shaken for 24 h. Then the filtrate was collected and the resin was rinsed several times with CH2Cl2 and MeOH. All the filtrates were combined and evaporated, and the resulting solid was dissolved in CH2Cl2. Amberlite IR-120 was introduced to the solution to take off remaining traces of DIEA. The mixture was stirred for a few minutes and filtered. The filtrate was evaporated to give compounds 2 to 19. Trituration in a minimum of cold ether was performed to obtain satisfying purity.
	Multi-step reaction with 3 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / -5 - 0 °C 2: formic acid / 2 h / 20 °C 3: iso-butanol / toluene / 20 °C
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C 2.1: formic acid / 2 h / 20 °C 2.2: 2 h / Reflux

	Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With benzotriazol-1-ol In dichloromethane; N,N-dimethyl-formamide at 0℃; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; Stage #3: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine Further stages;	4.2. Preparation of CDPs (3-35) General procedure: 4.2.1. Coupling of the first N-Boc protected α-aminoacid on oxime resinA desired quantity of oxime resin (1.12 mmol/g) wasadded to a peptide synthesis vessel. The resin was treatedthree times with CH2Cl2. Amino acid (3.0 equiv) and HOBt(3.0 equiv) were dissolved in DMF in a 100-mL flask andthe mixture was stirred for few minutes at 0 °C. DIC (3.0equiv), DIEA (3.0 equiv) and DMAP (0.1 equiv) wereadded and the mixture was introduced into the peptidesynthesis vessel and stirred mechanically for 3 h. Themixture was filtered under vacuum and the resin waswashed (DMF (3 × 100 mL), MeOH (3 × 100 mL), DMF(3 × 100 mL), MeOH (3 × 100 mL)) and dried under reducedpressure.4.2.2. Acetylation of unreacted sites on oxime resinThe resin was treated three times with DMF (3 × 50 mL).A solution of 50% v/v DMF/acetic anhydride (80 mL) andDIEA (1 mL) were added to the peptide synthesis vesseland shaken for 1 h. Then, the mixture was filtered undervacuum and the resin was washed (DMF (3 × 100 mL),MeOH (3 × 100 mL), DMF (3 × 100 mL), MeOH (3 × 100 mL))and dried under reduced pressure.4.2.3. Removal of the N-Boc protecting groupThe resin was treated three times with CH2Cl2 (100 mL). A50% v/v solution of TFA in CH2Cl2 was added to the peptidesynthesis vessel and shaken for 30 min. Then, the mixturewas filtered under vacuum and the resin was washed withDMF (3 × 100 mL), MeOH (3 × 100 mL), DMF (3 × 100 mL),MeOH (3 × 100 mL) and with a solution of 10% v/v DIEAin CH2Cl2 (100 mL).4.2.4. Coupling of the second N-Boc protectedα-amino acidThe amino acid (3.0 equiv) was dissolved in DMF in a100 mL flask. The solution was cooled to 0 °C, then HBTU(3.0 equiv) and HOBt (3.0 equiv) were added. The mixturewas poured into the peptide synthesis vessel in which theresin has been previously treated with CH2Cl2. DIEA (6.0equiv) was also added to the vessel and the mixture wasshaken for 3 h. After filtration under vacuum, the resinwas washed (DMF (3 × 100 mL), MeOH (3 × 100 mL), DMF(3 × 100 mL) and MeOH (3 × 100 mL)) and dried underreduce pressure. The Kaiser ninhydrin test was performedto monitor the efficiency of the coupling, and the couplingprocedure was repeated if needed.4.2.5. Cyclisation/cleavage from the resinFirst, N-Boc group was removed using procedure describedin (Section 4.2.3), but without the 10% v/v DIEA/CH2Cl2 washing step. After drying, CH2Cl2 and DIEA (2.5 equiv)were added to the peptide synthesis vessel and the mixturewas shaken for 2 min. Acetic acid (5.0 equiv) was thenadded and the content was shaken for 24 h. Then the filtratewas collected and the resin was rinsed several timeswith CH2Cl2 and MeOH. All the filtrates were combinedand evaporated, and the resulting solid was dissolved inCH2Cl2. Amberlite IR-120 was introduced to the solution toremove remaining traces of DIEA. The mixture was stirredfor a few minutes and filtered. The filtrate was evaporatedto give compounds 3 to 35. Trituration in a minimum ofcold ether was performed and led to desired compoundswith satisfying purity.
	Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Stage #2: With trifluoroacetic acid In dichloromethane for 0.5h; Stage #3: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine Further stages;	4.2 Preparation of CDPs (1-75) General procedure: 4.2.1. Coupling of the first N-Boc protected α-amino acid on oxime resinA desired quantity of oxime resin (1.12 mmol/g) was added to apeptide synthesis vessel. The resin was treated three times with CH2Cl2.Amino acid (3.0 equiv) and HOBt (3.0 equiv) were dissolved in DMF ina 100 mL flask and the mixture was stirred for few minutes at 0 °C. DIC(3.0 equiv), DIEA (3.0 equiv) and DMAP (0.1 equiv) were added andthe mixture was introduced into the peptide synthesis vessel and stirredmechanically for 3 h. The mixture was filtered under vacuum and theresin was washed [DMF (3×100 mL), MeOH (3×100 mL), DMF(3×100 mL), MeOH (3×100 mL)] and dried under reduced pressure.4.2.2. Acetylation of unreacted sites on oxime resinThe resin was treated three times with DMF (3×50 mL). A solutionof 50% (v/v) DMF/acetic anhydride (80 mL) and DIEA (1 mL) wereadded to the peptide synthesis vessel and shaken for 1 h. Then, themixture was filtered under vacuum and the resin was washed [DMF(3×100 mL), MeOH (3×100 mL), DMF (3×100 mL), MeOH(3×100 mL)] and dried under reduced pressure.4.2.3. Removal of the N-Boc protecting groupThe resin was treated three times with CH2Cl2 (100 mL). A 50% v/vsolution of trifluoroacetic acid (TFA) in CH2Cl2 was added to the peptidesynthesis vessel and shaken for 30 min. Then the mixture was filtered under vacuum and the resin was washed with DMF(3×100 mL), MeOH (3×100 mL), DMF (3×100 mL), MeOH(3×100 mL) and with a solution of 10% v/v DIEA in CH2Cl2 (100 mL).4.2.4. Coupling of the second N-Boc protected α-amino acidThe amino acid (3.0 equiv) was dissolved in DMF. The solution wascooled to 0 °C, then HBTU (3.0 equiv) and HOBt (3.0 equiv) wereadded. The mixture was poured into the peptide synthesis vessel inwhich the resin had been previously treated with CH2Cl2. DIEA (6.0equiv) was also added to the vessel and the mixture was shaken for 3 h.After filtration under vacuum, the resin was washed [DMF(3×100 mL), MeOH (3×100 mL), DMF (3×100 mL) and MeOH(3×100 mL)] and dried under reduce pressure. The Kaiser ninhydrintest was performed to monitor the efficiency of the coupling, and thecoupling procedure was repeated as needed.4.2.5. Cyclization/cleavage from the resinFirst, the N-Boc group was removed using the procedure describedin (4.2.3), but without the 10% v/v DIEA/CH2Cl2 washing step. Afterdrying, CH2Cl2 and DIEA (2.5 equiv) were added to the peptidesynthesis vessel and the mixture was shaken for 2 min. Acetic acid (5.0equiv) was then added and the content was shaken for 24 h. Then thefiltrate was collected and the resin was rinsed several times with CH2Cl2and MeOH. All filtrates were combined and evaporated, and the resultingsolid was dissolved in CH2Cl2. Amberlite IR-120 was introducedto the solution to remove the remaining traces of DIEA. The mixturewas stirred for a few minutes and filtered. The filtrate was evaporatedto give compounds 1 to 46. Trituration in a minimum of cold ether wasperformed and led to desired compounds with satisfying purity.
	Multi-step reaction with 3 steps 1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / N,N-dimethyl-formamide; acetonitrile / 16 h / 0 - 20 °C 2: formic acid / 20 °C 3: iso-butanol; toluene / 4 h / 90 °C
	Stage #1: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine With dmap; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With trifluoroacetic acid In dichloromethane for 0.5h; Stage #3: <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine Further stages;

Reference： [1]Bérubé, Christopher; Cardinal, Sébastien; Boudreault, Pierre-Luc; Barbeau, Xavier; Delcey, Nicolas; Giguère, Martin; Gleeton, Dave; Voyer, Normand [Tetrahedron, 2015, vol. 71, # 42, p. 8077 - 8084]
[2]Zhai, Huimin; Borzenko, Andrey; Lau, Ying Yin; Ahn, Shin Hye; Schafer, Laurel L. [Angewandte Chemie - International Edition, 2012, vol. 51, # 49, p. 12219 - 12223][Angew. Chem., 2012, vol. 124, # 49, p. 12219 - 12223,5]
[3]Current Patent Assignee: UNIVERSITY OF OXFORD; Oxford University Innovation (in: Oxford University) - WO2014/68341, 2014, A2
[4]Bérubé, Christopher; Barbeau, Xavier; Cardinal, Sébastien; Boudreault, Pierre-Luc; Bouchard, Corinne; Delcey, Nicolas; Lagüe, Patrick; Voyer, Normand [Supramolecular Chemistry, 2017, vol. 29, # 5, p. 330 - 349]
[5]Simon, Gaëlle; Bérubé, Christopher; Voyer, Normand; Grenier, Daniel [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 12, p. 2323 - 2331]
[6]Rajput, Sunnia; McLean, Kirsty J.; Poddar, Harshwardhan; Selvam, Irwin R.; Nagalingam, Gayathri; Triccas, James A.; Levy, Colin W.; Munro, Andrew W.; Hutton, Craig A. [Journal of Medicinal Chemistry, 2019, vol. 62, # 21, p. 9792 - 9805]
[7]Simon, Gaëlle; Bérubé, Christopher; Paquet-Côté, Pierre-Alexandre; Grenier, Daniel; Voyer, Normand [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 23]

81
S-Adenosyl-L-methionine [ No CAS ]
[ 2862-51-3 ]
(3S,6S)-3,6-dibenzyl-1-methylpiperazine-2,5-dione [ No CAS ]
[ 61125-52-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 31% 2: 11%	With potassium dihydrogenphosphate; D-Glucose; sodium phosphate dibasic dodecahydrate; S-adenosyl-L-methionine-dependent N-methyltransferase (Amir_4628); magnesium sulfate; ammonium chloride; sodium chloride; calcium chloride In water at 18 - 37℃; for 18h; Enzymatic reaction; regiospecific reaction;

Reference： [1]Giessen, Tobias W.; Von Tesmar, Alexander M.; Marahiel, Mohamed A. [Biochemistry, 2013, vol. 52, # 24, p. 4274 - 4283]

82
[ 2862-51-3 ]
[ 1609286-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 1.2: 12 h / 20 °C 2.1: triethylamine / toluene / 12 h / Reflux 3.1: diethyl ether / 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2

83
[ 2862-51-3 ]
[ 1609286-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 1.2: 12 h / 20 °C 2.1: triethylamine / toluene / 12 h / Reflux 3.1: diethyl ether / 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2

84
[ 2862-51-3 ]
[ 98778-70-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: (3S,6S)-3,6-dibenzylpiperazine-2,5-dione With borane-THF In tetrahydrofuran at 0℃; Reflux; Stage #2: With hydrogen bromide In acetic acid	17 (2S,5S)-2,5-Bis(phenylmethyl)piperazine dihydrobromide 19 To a vigorously stirred suspension of (3S,6S)-3,6-bis- (phenylmethyl)- piperazine-2,5- dione (1 .20 g, 5.10 mmol) in THF (26 mL) was added dropwise BH3 FontWeight="Bold" FontSize="10" THF (1 M solution in THF, 30 mL) at 0°C. The mixture was stirred for 1 h, slowly warming to r.t and heated to reflux for 2 h. The solution was filtered, cooled to 0°C, and 12% HBr/AcOH (10 mL) was slowly added. After stirring for 2 h, dry hexane was added and the solution was left to stand overnight in the freezer. The resulting dihydrobromide precipitates were collected by filtration, and then recrystallised from methanol/ether to give 19 as white solid (1 .20 g, 55%). IR (v, KBr/cm"1): 3300, 2700, 1455, 1070, 970, 740; H NMR (500 MHz, DMSO-d6) δ: 3.22-3.32 (overlap m, 8H, ArCH2, NHCH2), 3.89 (dq, J = 9.9, 5.0 Hz, 2H, NHCH), 7.30-7.43 (m, 10H, ArH), 9.40 (br s, 4H, NH); 3C NMR (125.8 MHz, DMSO-d6) δ: 33.8 (2 χ ArCH2), 40.7 (2 χ NHCH2), 51 .9 (2 χ NHCH), 127.4 (2 χ CH), 128.9 (4 χ CH) 129.4 (4 χ CH), 135.3 (2 x C); mp 226-228 °C; [a]22D -13.4 (c 2, H20); HRMS (Fl)+: m/z calcd for C18H24Br2N2 [M+ 426.0306, found 426.0286

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2 Location in patent: Page/Page column 37

85
[ 2862-51-3 ]
[ 141804-57-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 1.2: 12 h / 20 °C 2.1: triethylamine / toluene / 12 h / Reflux

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2

86
[ 2862-51-3 ]
[ 646994-91-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 1.2: 12 h / 20 °C 2.1: triethylamine / toluene / 12 h / Reflux

Reference： [1]Current Patent Assignee: Oxford University Innovation (in: Oxford University); UNIVERSITY OF OXFORD - WO2014/68341, 2014, A2

87
C₂₀H₂₄N₂O₅ [ No CAS ]
[ 2862-51-3 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: C₂₀H₂₄N₂O₅ With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 22h; Stage #2: With dmap In dichloromethane

Reference： [1]Funder, Erik Daa; Trads, Julie B.; Gothelf, Kurt V. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 185 - 198]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	2862-51-3	MDL No. :	MFCD00190985
Formula :	C₁₈H₁₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JUAPMRSLDANLAS-HOTGVXAUSA-N
M.W :	294.35	Pubchem ID :	76116
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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Code	Phrase
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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2862-51-3 ] {[proInfo.proName]}

Quality Control of [ 2862-51-3 ]

Related Doc. of [ 2862-51-3 ]

Product Details of [ 2862-51-3 ]

Safety of [ 2862-51-3 ]

Application In Synthesis of [ 2862-51-3 ]

[ 2862-51-3 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry