Name: 102849-49-0|(S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid|97%
Brand: Ambeed
SKU: A236920
Rating: 99 (35 reviews)

1
[ 143-16-8 ]
[ 102849-49-0 ]
N,N-dihexyl-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: dihexylamine In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

2
[ 771-61-9 ]
[ 102849-49-0 ]
(S)-2-(2-Oxo-pyrrolidin-1-yl)-butyric acid pentafluorophenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 1h;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

3
[ 4229-44-1 ]
[ 102849-49-0 ]
N-hydroxy-N-methyl-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: N-methylhydroxyamine hydrochloride In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

4
[ 593-56-6 ]
[ 102849-49-0 ]
N-methoxy-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: N-methoxylamine hydrochloride In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

5
[ 6638-79-5 ]
[ 102849-49-0 ]
N-methoxy-N-methyl-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

6
[ 74-89-5 ]
[ 102849-49-0 ]
N-methyl-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: methylamine In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

7
[ 100-46-9 ]
[ 102849-49-0 ]
N-benzyl-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: benzylamine In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

8
[ 102849-49-0 ]
(S)-2-(2-Oxo-pyrrolidin-1-yl)-butyric acid hydrazide [ No CAS ]
(2R)-2-(2-oxopyrrolidin-1-yl)butanohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10℃; for 0.5h; Stage #2: With hydrazine hydrate In dichloromethane at -10 - 20℃;

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

9
[ 873786-87-9 ]
[ 169221-12-9 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 250 mg 2: 140 mg	With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 0℃; for 7h;

Reference： [1]Boschi, Francesca; Camps, Pelayo; Comes-Franchini, Mauro; Munoz-Torrero, Diego; Ricci, Alfredo; Sanchez, Laura [Tetrahedron Asymmetry, 2005, vol. 16, # 22, p. 3739 - 3745]

10
[ 616-45-5 ]
[ 2681-94-9 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 2-pyrrolidinon With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Stage #2: (2R)-2-bromobutanoic acid In tetrahydrofuran at 20℃; for 16h;

Reference： [1]Boschi, Francesca; Camps, Pelayo; Comes-Franchini, Mauro; Munoz-Torrero, Diego; Ricci, Alfredo; Sanchez, Laura [Tetrahedron Asymmetry, 2005, vol. 16, # 22, p. 3739 - 3745]

11
[ 102849-49-0 ]
levetiracetam [ No CAS ]
[ 102767-28-2 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 3739 - 3745

12
[ 909566-58-1 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In phosphate buffer; acetonitrile at 25℃; for 6h;
87%	Stage #1: 1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; acetonitrile at 35℃; for 7h; Stage #2: With sodium hydroxide; sodium sulfite In aq. phosphate buffer; ethyl acetate; acetonitrile at 20℃; for 0.75h; Stage #3: With hydrogenchloride In aq. phosphate buffer; ethyl acetate	4.1.6 (S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid (S)-8 A mixture of (S)-7 (1.00 g, 6.3 mmol), TEMPO (0.04 g, 0.31 mmol), acetonitrile (20 mL), and sodium phosphate buffer (9 mL, 0.67 M, pH 6.7) was heated to 35 °C. Sodium chlorite (0.6 g dissolved in 2 mL water, 6.4 mmol) and dilute bleach (4-6%, 2 mL diluted in 4 mL water) were then added simultaneously over 1 h. The reaction mixture was stirred at 35 °C until the reaction was complete (6 h, TLC), then cooled to room temperature. Water (20 mL) was added and the pH was adjusted to 8 with 2 M NaOH. The reaction was quenched by pouring into an ice cold Na2SO3 solution maintained at °C. After stirring for 30 min at room temperature, ethyl acetate (20 mL) was added and continued the stirring for an additional 15 min. The organic layer was separated and discarded. More ethyl acetate (20 mL) was added, and the aqueous layer was acidified with 2 M HCl to pH 3-4. The organic layer was separated, washed with water (2 × 15 mL), brine (20 mL), and concentrated under reduced pressure to afford the carboxylic acid (S)-8 (0.94 g, 87%); [α]D25=-27.1 (c 1.1, CHCl3) {lit.7a [α]D25=-23.6 (c 0.97, CHCl3)}; IR (CHCl3): 3444, 3020, 1646, 1422, 1215, 1122, 1043, 929, 759 cm-1; 1H NMR (200 MHz, CDCl3): δH = 0.94 (t, J = 7.3 Hz, 3H), 1.64-1.81 (m, 2H), 2.01-2.18 (m, 2H), 2.50 (t, J = 7.7 Hz, 2H), 3.31-3.42 (m, 1H), 3.50-3.62 (m, 1H), 4.61-4.69 (dd, J = 10.7, 5 Hz, 1H); 13C NMR (50 MHz, CDCl3): δC = 177.1 (CO), 174.4 (CO), 55.5 (CH), 43.9 (CH2), 30.8 (CH2), 21.9 (CH2), 18.2 (CH2), 10.8 (CH3); MS: m/z 171 [M]+, 194 [M+Na]+.
84%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate In water; acetonitrile at 40℃; for 91h; aq. phosphate buffer;

76%	With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In dichloromethane; water at 20℃; for 12.5h;	2 Step-2: Synthesis of Compound 4 Aqueous potassium hydroxide (0.017 mol in 10 ml water), tetra-n-butyl ammonium bromide (0.0062 mol) and compound 3 (0.0063 mol) in DCM (10 ml) was stirred for 30 min at room temperature and then added potassium permanganate (0.094 mol) and continued the stifling. After completion of reaction filtered through celite bed and washed with water (10 ml). The aqueous later PH was adjusted to 3 using HCl (2 ml), added sodium phosphate (0.0152 mol) and toluene (25 ml). The reaction mixture was extracted with DCM (2×25 ml). The organic layer was dried with Na2SO4 and distilled under reduced pressure to compound 4 as oil. To this toluene (10 ml) was added and stirred at 0° C. for about 30 min. The solid was filtered and washed with toluene (5 ml) to afford the pure compound 4.
54%	With potassium permanganate; water; sodium carbonate at 0 - 20℃; for 18 - 19h;	2 A mixture of 225 g of (S)-α- ethyl -2-oxo pyrrolidine ethanol and a solution of 44.8 g of sodium carbonate in 4500 ml of water placed in a 10 litre round bottomed flask. Then 340 EPO g of potassium permanganate is added to the reaction mixture with vigorous stirring, during 3-4 hours, cooling the mixture to 0°-5°C by immersing in a bath of ice water. Allow the reaction mixture to attain room temperature gradually. 15 hours later, filter off the precipitated manganese dioxide, concentrated the filtrate to about 1000 ml under reduced pressure and acidified with dilute sulphuric acid up to pH 2 followed by the saturation with NaCl. Cover the solution with a layer of dichloromethane. Separate the dichloromethane layer and extract the aqueous layer two to three times with 100 ml portions of dichloromethane and distilled off on rotavapor. Recrystallised the crude acid (209 g) from 210 ml of toluene; filter and wash with toluene . Yield : 130 gm (54 %) ; MP 1240C ; [oc]25= -24.32 (c=l, acetone)
	Stage #1: 1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one With potassium hydroxide In dichloromethane at 10℃; for 0.166667h; Stage #2: With potassium permanganate In dichloromethane at 30℃; for 8h; Stage #3: With hydrogenchloride; water at 0℃; for 0.0833333h;	3 EXAMPLE 3: PREPARATION OF (S)-α-ETHYL-2-OXO PYRROLIDINE ACETIC ACID (FORMULA II)Potassium hydroxide (10 g) was dissolved into water (180 ml) and cooled to a temperature of about 1 O0C. Tetra-n-butyl ammonium bromide (2 g) and (S)- α-ethyl-2-oxo pyrrolidine ethanol (10 g) in methylene chloride (18 ml) were charged followed by stirring for about 10 minutes. Potassium permanganate (15 g) was charged followed by stirring at a temperature of about 300C for about 8 hours. The resultant reaction mixture was filtered through a celite bed and the celite was washed with water (100 ml) followed by separation of organic and aqueous layers. The separated aqueous layer was charged into a clean and dry round bottom flask followed by cooling to about 0°C. pH of the reaction solution was adjusted to about 3 by the addition of hydrochloric acid (2 ml) followed by stirring for about 5 minutes. To the resultant reaction mixture sodium phosphate (25 g) was added followed by stirring for about 10 minutes. Toluene (150 ml) was added into the reaction solution and about 50% of the solvent was distilled off. The resultant reaction solution was extracted with dichloromethane (5*50 ml) followed by separation of organic and aqueous layers. The organic layer was dried over anhydrous sodium sulphate (10 g). Organic layer was distilled completely at a temperature of about 300C under vacuum to obtain the title compound as a residue.To the residue toluene (10 ml) was added and stirred at 0°C for about 30 minutes. The separated solid was filtered and the solid was washed with toluene (5 ml). The obtained solid was dried at a temperature of about 600C under vacuum for about 1 hour to afford the pure 5 3 fj ϖf title compound.Purity by HPLC: 97%.
92 %Spectr.	With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; water In aq. buffer for 0.6h; Electrolysis;

Reference： [1]Kotkar, Shriram P.; Sudalai, Arumugam [Tetrahedron Letters, 2006, vol. 47, # 38, p. 6813 - 6815]
[2]Mujahid, M.; Mujumdar, P.; Sasikumar, M.; Kunte, S. S.; Muthukrishnan, M. [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515,4] Mujahid; Mujumdar; Sasikumar; Kunte; Muthukrishnan [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515]
[3]Location in patent: experimental part Imahori, Tatsushi; Omoto, Keisuke; Hirose, Yumi; Takahata, Hiroki [Heterocycles, 2008, vol. 76, # 2, p. 1627 - 1632]
[4]Current Patent Assignee: CELLIXBIO PRIVATE LTD - US9290486, 2016, B1 Location in patent: Page/Page column 37
[5]Current Patent Assignee: LUPIN LIMITED - WO2006/95362, 2006, A1 Location in patent: Page/Page column 5; 7-8
[6]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2008/77035, 2008, A2 Location in patent: Page/Page column 8; 14-15
[7]Zhong, Xing; Hoque, Md Asmaul; Graaf, Matthew D.; Harper, Kaid C.; Wang, Fei; Genders, J. David; Stahl, Shannon S. [Organic Process Research and Development, 2021, vol. 25, # 12, p. 2601 - 2607]

13
[ 102849-49-0 ]
[ 102767-28-2 ]

Yield	Reaction Conditions	Operation in experiment
78.4%		Example 1 (Invention) Step 1 (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid (150 g, 0.87 mol) was dissolved in methanol (235 g, 300 ml) at 45C and thionyl chloride (56 g, 0.47 mol) was added dropwise over 30 min. The reaction mixture was stirred at 45C for additional 15-30 min until complete conversion of (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid was observed via HPLC (unreacted (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid ? 2%, by HPLC % area). At reaction completed, the volatiles were distilled off at moderate temperature and reduced pressure (35-40C, 150-200 mbar) until 10% of the whole volume was eliminated, then the mixture was reintegrated with fresh methanol up to initial volume. After that, the reaction mixture was neutralized by bubbling ammonia gas at 20C up to a pH value equal to about 5, and stirred at 20C for 1 h. A limited amount of salts (about 44 g) precipitated and was filtered off. The resulting methanol solution was directly transferred to the autoclave.Step 2 The reaction mixture was pressurized up to about 3 bar with ammonia gas at 20C, and stirred until complete conversion to (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide was observed via HPLC. Then, once the reaction mixture was taken out of the autoclave, the residual salts formed (about 20 grams) were filtered off and the methanol solution was distilled up to a minimum volume at moderate temperature and reduced pressure (35- 40C, 150 - 200 mbar). Acetone (115 ml) was added and the mixture was distilled again at moderate temperature and reduced pressure (35-40C, 150-200 mbar) to minimum volume. After that acetone (300 ml) was charged over the residue and the mixture was heated and refluxed for 30 minutes. Finally, the solution was cooled down slowly to 0C and crude levetiracetam was isolated by filtration. Crude levetiracetam (molar yield 73.1 %, (R)-enantiomer: 1.171 %) was then submitted to a final purification process in one step to give pure levetiracetam. Acetone (750 ml) was charged over crude levetiracetam and the mixture was again stirred and heated to reflux. Once refluxed for about 30 minutes the hot mixture was filtered to remove residual salts and cooled slowly to 0C. Pure levetiracetam ((R)-enantiomer: 0.01%) was obtained by filtration and drying under vacuum at 40C. Overall molar yield was 60.0 % by mole of the starting amount of (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid (ponderal yield 78.4 % by weight).
65%	With ammonium hydroxide; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; water; at 0 - 20℃; for 12.5h;	To a cold 0 C. solution of acid 4 (0.292 mol) and Et3N (0.307 mol) in anhydrous THF (20 ml) was added ethyl chloroformate (0.304 mol) and the mixture stirred at 0 C. for 30 min. Ammonium hydroxide (25% w/v aqueous solution, 19 ml, 136.0 mol) was added and the reaction mixture was stirred at room temperature for 12 h. After the addition of K2CO3 (30.0 mol), the mixture was filtered and the volatile material (solvent and Et3N) distilled off in vacuo. The solid residue was extracted with DCM (3×50 ml) and combined extracts were dried over Na2SO4 and concentrated in vacuo, recrystallization from acetone gave compound 5 as white solid.
		EXAMPLE 1Preparation of Crude Levetiracetam[0032] 75 parts by weight (pbw) of (S)-alpha-ethyl-2-oxo-l-pyrrolidineacetic acid(levo acid) is charged to a dry flask equipped with means for establishing a nitrogen atmosphere, with a mechanical stirrer and with a cooling bath. About 373 pbw of acetonitrile is added and the mixture is stirred at a temperature of 10 - 15 0C under a nitrogen atmosphere. A suspension is formed. About 105 pbw of DiBOC is added to the suspension and is stirred at a temperature of 10 - 15 0C. Thereafter, 42 pbw of ammonium bicarbonate is added to the mixture with further stirring at a temperature of 10 - 15 0C. Finally, about 21 pbw of pyridine is added to the mixture and the resulting mixture is stirred at a temperature of 10 - 20 0C. As the reaction progresses, CO2 gas is generated and the suspension gradually becomes a solution. The reaction temperature should be controlled such that it does not exceed 20 0C. Higher temperatures lead to undesired racemization.

Reference： [1]Patent: EP2147911,2010,A1 .Location in patent: Page/Page column 5
[2]Tetrahedron Letters,2006,vol. 47,p. 6813 - 6815
[3]Heterocycles,2008,vol. 76,p. 1627 - 1632
[4]Patent: US9290486,2016,B1 .Location in patent: Page/Page column 38
[5]Organic and Biomolecular Chemistry,2019,vol. 17,p. 2770 - 2775
[6]Patent: WO2006/127300,2006,A1 .Location in patent: Page/Page column 7
[7]Journal of the American Chemical Society,2017,vol. 139,p. 13944 - 13949

14
[ 1004767-63-8 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
48.7%	Stage #1: (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amide With sulfonic acid type-ion exchange resin; water In toluene at 110℃; for 6h; Stage #2: With sodium carbonate In water; toluene Stage #3: With hydrogenchloride; water	5 Example 5; (-)-(S)-alpha-ethyl-2-oxo-l-pyrrolidineacetic acid.; In a 25 ml flask equipped with mechanical stirring and bubble condenser, 1.0 g of (-)-(S)-alpha-ethyl-2-oxo- 1 -pyrrolidineacet-N-(+)-(R)-( 1 -phenylethyl)-amide (3.65 mmol, d.e.= 98%), 7.3 g of p-toluensulfonic acid supported by polymeric matrix (30.00-60.00 mesh, 2.0-3.0 mmol/g), 0.263 ml of water (14.60 mmol) and 14.5 ml of toluene were charged under nitrogen atmosphere. Reaction mixture was heated up to 1100C temperature by oil bath and maintained at reflux temperature up to complete disappearing of starting material (about 6 h; checked by HPLC). Reaction checks were made by taking both a portion of liquid phase and an amount of resin; mixture was filtered, washed with about 2 ml of an ammonia solution (7.0 M in MeOH) and solvent was eliminated under vacuum. At complete conversion, reaction mixture was filtered on gootch, resin was washed with aqueous NaOH IM (2 x 15 ml) and 10 ml of toluene. Phases were separated and toluene solution was washed with 15 ml of soda 1 M in water up to pH value around 10-12. So obtained aqueous basic phase was further washed with 20 ml of toluene and then acidified with 3% aqueous HCl up to pH value around 1. Aqueous acid solution was extracted with dichloromethane (5 x 50 ml). Collected organic phases were dried on Na2SO4, and concentrated under vacuum up to a residue was formed. So obtained white solid was dried under vacuum at 25°C temperature overnight to give 304.0 mg of the title compound (1.78 mmol, 48.7% yield, e.e.= 91.9%).

Reference： [1]Current Patent Assignee: GEFIM S.P.A. - WO2008/12268, 2008, A1 Location in patent: Page/Page column 18-19

15
[ 67-56-1 ]
[ 102849-49-0 ]
[ 358629-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 20 - 65℃; for 2.5h;	6 Example 6; (-)-(S)-alpha-ethyl-2-oxo-l-pyrrolidineacetamide (levetiracetam).; In a 25 ml flask equipped with thermometer, mechanical stirring and bubble condenser, 3.344 g of (-)-(S)-alpha-ethyl-2-oxo-l-pyrrolidineacetic acid (19.58 mmol, e.e.= 95.0%), 0.11 ml of concentrated sulfuric acid (95.6% m/m, 1.97 mmol) and 17 ml of methanol were charged under nitrogen atmosphere at room temperature. Reaction mixture was heated up to 65°C temperature by oil bath and maintained at reflux temperature up to complete disappearing of starting material (about 2.5 h; checked by TLC, Rf = 0.58 CH2Cl2:Me0H:Ac0H 80:20: 1/silica gel). Reaction mixture was concentrated under vacuum up to a residue was formed then water (2.0 ml) was added. In a 25 ml flask equipped with magnetic stirring and condenser, 7.5 ml of 30% aqueous ammonia solution was charged and cooled to 00C temperature and, keeping under stirring, the aqueous solution of crude (-)-(S)-alpha-ethyl-2-oxo- 1-pyrrolidineacetic acid methyl ester was charged dropwise. When addition was completed, reaction mixture was thermostabilized at 200C and said conditions were maintained overnight.At complete conversion (about 10 h) excess of ammonia was eliminated by vacuum evaporator. Reaction mixture was extracted with dichloromethane (2 x 3.5 ml), transferred into a continuous liquid-liquid extractor and then refluxed with 7 ml of dichloromethane for 6 hours. Collected organic phases were concentrated under vacuum up to a residue was formed. 2.666 g of a yellow solid was obtained which was suspended in 15.0 ml of acetone. Reaction mixture was heated up to 600C temperature so that complete dissolution of the solid was reached. Then, mixture was slowly cooled. White solid was isolated by filtration, washed with mother liquors and then with 3 ml of cold acetone and, finally, dried in oven under vacuum at 400C temperature for 4 hours to give 2.259 g of levetiracetam (13.274 mmol, 67.8% yield, e.e. 99.9%).
	Stage #1: methanol; (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid at 45℃; for 24h; Stage #2: With ammonia In methanol at 20℃; for 1h;	4.1 EXAMPLE 4Effect of Activating Agent AmountExample 1 was repeated using different amount of thionyl chloride as reported in the following Table 1. The amount of thionyl chloride is expressed in terms of equivalent with respect to (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid.The data of Table 1 clearly show that the use of a substoichiometric amount of thionyl chloride (samples 2 to 5) does not substantially affect the conversion time and conversion yield of (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidine acetic acid. On the contrary, the use of catalytic amount of thionyl chloride (samples 6 and 7) substantially increases the conversion time and/or the conversion yield.

Reference： [1]Current Patent Assignee: GEFIM S.P.A. - WO2008/12268, 2008, A1 Location in patent: Page/Page column 19-20
[2]Current Patent Assignee: GEFIM S.P.A. - US2011/65932, 2011, A1 Location in patent: Page/Page column 4

16
[ 912643-33-5 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 97 percent / hydrogen / Pd/C / methanol / 6 h / 760 Torr 2: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; sodium hypochlorite; sodium chlorite / acetonitrile; aq. phosphate buffer / 6 h / 25 °C / pH 6.8
	Multi-step reaction with 2 steps 1.1: palladium(II) hydroxide; hydrogen / methanol / 24 h / 20 °C / 3102.97 Torr 2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 7 h / 35 °C / pH 6.7 2.2: 0.75 h / 20 °C / pH 8 2.3: pH 3 - 4

Reference： [1]Kotkar, Shriram P.; Sudalai, Arumugam [Tetrahedron Letters, 2006, vol. 47, # 38, p. 6813 - 6815]
[2]Mujahid, M.; Mujumdar, P.; Sasikumar, M.; Kunte, S. S.; Muthukrishnan, M. [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515,4] Mujahid; Mujumdar; Sasikumar; Kunte; Muthukrishnan [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515]

17
[ 67118-31-4 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.33 h / 0 °C 1.2: 24 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / -78 °C 2.1: 140 mg / LiOH*H₂O; H₂O₂ / tetrahydrofuran / 7 h / 0 °C
	Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 80 - 90 °C 2.1: sodium hydroxide; water / 0.5 h / 0 - 10 °C 2.2: pH 4 - 5

Reference： [1]Boschi, Francesca; Camps, Pelayo; Comes-Franchini, Mauro; Munoz-Torrero, Diego; Ricci, Alfredo; Sanchez, Laura [Tetrahedron Asymmetry, 2005, vol. 16, # 22, p. 3739 - 3745]
[2]Current Patent Assignee: SHANDONG POLYTECHNIC COLLEGE - CN110590635, 2019, A

18
[ 102849-49-0 ]
N-hydroxy-2-(2-oxo-pyrrolidin-1-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DCC / tetrahydrofuran / 1 h / 0 °C 2: 0.85 g / (NH₂OH)2*H₂SO₄; Et₃N / tetrahydrofuran / 21 h / 0 - 20 °C

Reference： [1]Kenda, Benoit M.; Matagne, Alain C.; Talaga, Patrice E.; Pasau, Patrick M.; Differding, Edmond; Lallemand, Bénédicte I.; Frycia, Anne M.; Moureau, Florence G.; Klitgaard, Henrik V.; Gillard, Michel R.; Fuks, Bruno; Michel, Philippe [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 530 - 549]

19
[ 67-56-1 ]
[ 102849-49-0 ]
(S)-α-ethyl-2-oxo pyrrolidine acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ion exchange resin 225H⁺ for 12h; Heating / reflux;	3 Preparation of (S)-α-ethyl-2-oxo pyrrolidine acetic acid methyl ester (V) A mixture of 34 g (S)-α-ethyl-2-oxo pyrrolidine acetic acid and 100 ml of methanol was taken in a 250 ml of round bottom flask fitted with reflux condenser and added 3.4 g ion exchange resin 225H^tO the reaction. Allowed to reflux for 12 hours. Filter the resin. The crude product in methanol was taken as such for ammonolysis.

Reference： [1]Current Patent Assignee: LUPIN LIMITED - WO2006/95362, 2006, A1 Location in patent: Page/Page column 5; 8

20
[ 124-63-0 ]
[ 102849-49-0 ]
C₉H₁₅NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0℃; for 0.5h;	1 EXAMPLE 1; Preparation of (0C and triethylamine (53 g, 0.53 mol) and methanesulfonyl chloride (39 g, 0.34 mol) were added dropwise. The mixture was stirred at 0 0C for 30 min., then a stream of ammonia was purged in the solution for 2 hours. The insoluble solids were filtered and the filtrate was concentrated. The product was crystallized from methyl isobutyl ketone to give 36 g (80 %) of (

Reference： [1]Current Patent Assignee: APOTEX INC - WO2006/53441, 2006, A1 Location in patent: Page/Page column 12-13

21
[ 102916-46-1 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride In water	3 EXAMPLE 3; Preparation of (ιS)-alpha-Ethyl-2-oxo-l-pyrrolidineacetic acid (i?)-alpha- methylbenzylamine salt; A solution of (i?)-alpha-methylbenzylamine (106 g) and triethylamine (89 g) in toluene (100 ml) was added to a suspension of (i?iS)-alpha-ethyl-2-oxo-l- pyrrolidineacetic acid (300 g, 1.75 mol) in toluene (IL). The mixture was heated until complete dissolution, cooled to room temperature and stirred for 3 hours. The solids were filtered and rinsed with toluene (300 ml) to give 250 g of (iS)-alpha-ethyl-2-oxo-l- pyrrolidineacetic acid (i?)-alpha-methylbenzylamine salt. The solids were crystallized from toluene and 205 g (yield 41%) of ()S)-alpha-ethyl-2-oxo-l -pyrrolidineacetic acid (i?)-alpha-methylbenzylamine salt was obtained. The isolated solid was treated with hydrochloric acid solution and the enantiomerically pure (iS)-alpha-ethyl-2-oxo-l~ pyrrolidineacetic acid could be isolated in 90% yield.
87.1%	Stage #1: (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt With water; sodium hydroxide at 0 - 10℃; for 0.5h; Stage #2: With hydrogenchloride In water	1.3 3) Step 4 70.3 g of white solid obtained in step 3 was added to water (2 mL/g), at 0-10 ° C, add 30% NaOH solution dropwise to pH = 4-5, and stir for 0.5h. Toluene (3mL/g) was added for extraction, and the aqueous phase was reduced to 0-10 ° C. Add concentrated hydrochloric acid dropwise to pH = 4-5, precipitate a solid, CH2Cl2 (3 mL/g × 2) was added for extraction, and the organic phase was concentrated in vacuo at 40 ° C to dryness to obtain 36 g of a crude product. EtOH (1.5 mL/g crude) was added to the crude product, and the temperature was raised to 70 ° C with stirring to dissolve, reduce to 0-10 , keep warm for 2h, suction filter, vacuum drying at 40 ° C for 4h to obtain the product (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid, white solid (35.79 g, 87.1%).

Reference： [1]Current Patent Assignee: APOTEX INC - WO2006/53441, 2006, A1 Location in patent: Page/Page column 13
[2]Current Patent Assignee: SHANDONG POLYTECHNIC COLLEGE - CN110590635, 2019, A Location in patent: Paragraph 0043; 0052-0055

22
C₈H₁₁N*C₈H₁₃NO₃ [ No CAS ]
[ 102916-46-1 ]
[ 103833-72-3 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₈H₁₁N*C₈H₁₃NO₃; (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt With sodium hydroxide In water at 20℃; for 0.5h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 2h; Stage #3: With acetic anhydride In toluene at 20℃; for 12h; Heating / reflux;	4 EXAMPLE 4; Recovery and epimerization of (i?)-alpha-ethyl-2-oxo~l-pyrrolidineacetic acid from the mother liquor; The combined mother liquors from above were concentrated to half volume and water (200 ml) and 50% sodium hydroxide (52 g) were added sequentially and the, mixture was stirred at 2O0C for 30 min. and then was separated. The aqueous layer was washed with toluene (150 ml), acidified with 32% hydrochloric acid until pH= 2-3. The resulting suspension was cooled to 0-50C and stirred for 2 h. The solids were collected by filtration, and were rinsed with cold water. The damp solids were dried under vacuum oven at 40-500C for 4h to give 16Og of (i?)-enriched ethyl-2-oxo-l- pyrrolidineacetic acid. To the above solids, toluene (640 ml) and acetic anhydride (145 g) were added and the mixture was heated to reflux for 1O h. The solution was cooled to 2O0C and stirred for another 2h. The solids were collected by filtration and rinsed with toluene (150 ml) to give (i?1S)-alpha-ethyl-2-oxo-l-pyrrolidineacetic acid (152 g).

Reference： [1]Current Patent Assignee: APOTEX INC - WO2006/53441, 2006, A1 Location in patent: Page/Page column 14

Yield	Reaction Conditions	Operation in experiment
94.5%		1.b (b) (b) Preparation of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid 5.04 kg of the salt obtained in (a) above are dissolved in 9 liters of water. 710 g of a 30% sodium hydroxide solution are added slowly so that the pH of the solution reaches 12.6 and the temperature does not exceed 25° C. The solution is stirred for a further 20 minutes and the alpha-methylbenzylamine liberated is extracted with a total volume of 18 liters of benzene. The aqueous phase is then acidified to a pH of 1.1 by adding 3.2 liters of 6N hydrochloric acid. The precipitate formed is filtered off, washed with water and dried. The filtrate is extracted repeatedly with a total volume of 50 liters of dichloromethane. The organic phase is dried over sodium sulfate and filtered and evaporated to dryness under reduced pressure. The residue obtained after the evaporation and the precipitate isolated previously, are dissolved together in 14 liters of hot dichloromethane. The dichloromethane is distilled and replaced at the distillation rate, by 14 liters of toluene from which the product crystallizes. The mixture is cooled to ambient temperature and the crystals are filtered off to obtain 2.78 kg of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid. Melting point: 125.9° C. [alpha]D20 =-26.4° (c=1, acetone). Yield: 94.5%.

24
[ 541-41-3 ]
[ 102849-49-0 ]
[ 102767-28-2 ]

Yield	Reaction Conditions	Operation in experiment
72.3%	With ammonia; triethylamine; In molecular sieve; dichloromethane; ethyl acetate; toluene;	(c) Preparation of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide 34.2 g (0.2 mole) of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid are suspended in 225 ml of dichloromethane cooled to -30 C. 24.3 g (0.24 mole) of triethylamine are added dropwise over 15 minutes. The reaction mixture is then cooled to -40 C. and 24.3 g (0.224 mole) of ethyl chloroformate are added over 12 minutes. Thereafter, a stream of ammonia is passed through the mixture for 41/2 hours. The reaction mixture is then allowed to return to ambient temperature and the ammonium salts formed are removed by filtration and washed with dichloromethane. The solvent is distilled off under reduced pressure. The solid residue thus obtained is dispersed in 55 ml toluene and the dispersion is stirred for 30 minutes and then filtered. The product is recrystallized from 280 ml of ethyl acetate in the presence of 9 g of 0,4 nm molecular sieve in powder form. 24.6 g of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide are obtained. Melting point: 115-118 C. [alpha]D25 =-89.7 (c=1, acetone). Yield: 72.3%. Analysis for C8 H14 N2 O2 in %: calculated: C, 56.45; H, 8.29; N, 16.46; found: C, 56.71; H, 8.22; N, 16.48.

Reference： [1]Patent: US4696943,1987,A

25
[ 102849-49-0 ]
[ 1034332-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane at -25 - -15℃; for 1.66667h;	4 EXAMPLE 3: PREPARATION OF (S)-α-ETHYL-2-OXO PYRROLIDINE ACETIC ACID (FORMULA II)Potassium hydroxide (10 g) was dissolved into water (180 ml) and cooled to a temperature of about 1 O0C. Tetra-n-butyl ammonium bromide (2 g) and (S)- α-ethyl-2-oxo pyrrolidine ethanol (10 g) in methylene chloride (18 ml) were charged followed by stirring for about 10 minutes. Potassium permanganate (15 g) was charged followed by stirring at a temperature of about 300C for about 8 hours. The resultant reaction mixture was filtered through a celite bed and the celite was washed with water (100 ml) followed by separation of organic and aqueous layers. The separated aqueous layer was charged into a clean and dry round bottom flask followed by cooling to about 0°C. pH of the reaction solution was adjusted to about 3 by the addition of hydrochloric acid (2 ml) followed by stirring for about 5 minutes. To the resultant reaction mixture sodium phosphate (25 g) was added followed by stirring for about 10 minutes. Toluene (150 ml) was added into the reaction solution and about 50% of the solvent was distilled off. The resultant reaction solution was extracted with dichloromethane (5*50 ml) followed by separation of organic and aqueous layers. The organic layer was dried over anhydrous sodium sulphate (10 g). Organic layer was distilled completely at a temperature of about 300C under vacuum to obtain the title compound as a residue.To the residue toluene (10 ml) was added and stirred at 0°C for about 30 minutes. The separated solid was filtered and the solid was washed with toluene (5 ml). The obtained solid was dried at a temperature of about 600C under vacuum for about 1 hour to afford the pure 5 3 fj ϖf title compound.Purity by HPLC: 97%.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2008/77035, 2008, A2 Location in patent: Page/Page column 15

26
[ 358629-39-7 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(norbornadiene)rhodium(l)tetrafluoroborate; C₆₀H₄₆O₄P₂; hydrogen In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction;

Reference： [1]Etayo, Pablo; Nunez-Rico, Jose Luis; Fernandez-Perez, Hector; Vidal-Ferran, Anton [Chemistry - A European Journal, 2011, vol. 17, # 50, p. 13978 - 13982]

27
[ 1415316-37-8 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 2.1: palladium(II) hydroxide; hydrogen / methanol / 24 h / 20 °C / 3102.97 Torr 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 7 h / 35 °C / pH 6.7 3.2: 0.75 h / 20 °C / pH 8 3.3: pH 3 - 4

Reference： [1]Mujahid, M.; Mujumdar, P.; Sasikumar, M.; Kunte, S. S.; Muthukrishnan, M. [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515,4] Mujahid; Mujumdar; Sasikumar; Kunte; Muthukrishnan [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515]

28
[ 13932-53-1 ]
[ 102849-49-0 ]
C₁₁H₁₇NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	4.1.7 (S)-2-(2-Oxopyrrolidin-1-yl)butanamide (levetiracetam) 1 To a solution of acid (S)-8 (0.70 g, 4.1 mmol) and triethylamine (0.7 mL, 4.9 mmol) in dry THF (10 mL) was added ethyl chloroformate (0.4 mL, 4.5 mmol) at 0 °C under an argon atmosphere. After 1 h, ammonium hydroxide (25% w/v aqueous solution, 2.8 mL, 20.4 mmol) was added and the mixture was stirred at ambient temperature for another 16 h. After completion of the reaction, potassium carbonate (0.8 g, 6 mmol) was added and the reaction mixture was filtered, and washed with ethyl acetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, dichloromethane/methanol, 95:5) to yield 1 as a pale yellow solid (0.56 g, 80%).

Reference： [1]Mujahid, M.; Mujumdar, P.; Sasikumar, M.; Kunte, S. S.; Muthukrishnan, M. [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515,4]

29
[ 541-41-3 ]
[ 102849-49-0 ]
C₁₁H₁₇NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	4.1.7 (S)-2-(2-Oxopyrrolidin-1-yl)butanamide (levetiracetam) 1 To a solution of acid (S)-8 (0.70 g, 4.1 mmol) and triethylamine (0.7 mL, 4.9 mmol) in dry THF (10 mL) was added ethyl chloroformate (0.4 mL, 4.5 mmol) at 0 °C under an argon atmosphere. After 1 h, ammonium hydroxide (25% w/v aqueous solution, 2.8 mL, 20.4 mmol) was added and the mixture was stirred at ambient temperature for another 16 h. After completion of the reaction, potassium carbonate (0.8 g, 6 mmol) was added and the reaction mixture was filtered, and washed with ethyl acetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, dichloromethane/methanol, 95:5) to yield 1 as a pale yellow solid (0.56 g, 80%).
	With triethylamine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;

Reference： [1]Mujahid; Mujumdar; Sasikumar; Kunte; Muthukrishnan [Tetrahedron Asymmetry, 2012, vol. 23, # 20-21, p. 1512 - 1515]
[2]Liniger, Marc; Liu, Yiyang; Stoltz, Brian M. [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13944 - 13949]

30
[ 102849-49-0 ]
[ 543-27-1 ]
C₁₂H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With triethylamine In dichloromethane at 0℃; Inert atmosphere; Stage #2: isobutyl chloroformate In dichloromethane for 1h; Inert atmosphere;

Reference： [1]Cai, Hancheng; Mangner, Thomas J.; Muzik, Otto; Wang, Ming-Wei; Chugani, Diane C.; Chugani, Harry T. [ACS Medicinal Chemistry Letters, 2014, vol. 5, # 10, p. 1152 - 1155]

31
[ 102849-49-0 ]
(2S,7‴R,11‴R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 °C 2: dichloromethane / 72 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITAT DE BARCELONA - WO2014/206877, 2014, A1

32
[ 102849-49-0 ]
(+)-(αS,7R,11R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0.5 h / 0 °C 2: dichloromethane / 72 h / 0 - 20 °C 3: hydrogenchloride / dichloromethane; methanol

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITAT DE BARCELONA - WO2014/206877, 2014, A1

33
[ 541-41-3 ]
[ 102849-49-0 ]
C₉H₁₂ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0℃; for 0.5h;	9 Example 9 A solution of (S)-2-(2-oxopyrrolidin-1 -yl)butanoic acid (I la) (99 mg, 0.58 mmol) in anhyd. CH2CI2(6 mL) was cooled to 0 °C with an ice bath, and treated dropwise with anhyd. Et3N (0.16 mL, 1 17 mg, 1.16 mmol) and ethyl chloroformate (0.05 mL, 62.8 mg, 0.58 mmol). The resulting mixture was stirred at 0 °C for 30 min and treated with a solution of amine (+)-(7 1 1 R)-(llla) (230 mg, 0.58 mmol) in anhyd. CH2CI2(5 mL). The reaction mixture was stirred at room temperature for 3 days and treated with 10% aq Na2C03(40 mL). The phases were separated and the aqueous phase was further extracted with CH2CI2(3 x 30 mL). The combined organic extracts were dried with anhyd. Na2S04, filtered, and evaporated under reduced pressure to give a crude product (343 mg), which was subjected to column chromatography [40-60 μηη silica gel (10 g), CH2Cl2/MeOH/50% aq NH4OH mixtures]. On elution with CH2CI2/MeOH/50% aq NH4OH 99.95:0.05:0.2, the compound of the title (176 mg, 56% yield) was isolated as a yellowish solid. The isolated compound of the title was transformed into the corresponding hydrochloride as follows: A solution of the free base (176 mg, 0.32 mmol) in CH2CI2(15 mL) was filtered through a 0.2 μηι NYL filter and treated with a 0.53 N methanolic solution of HCI (2.7 mL, 1 .43 mmol). The solution was concentrated in vacuo to dryness and the solid residue was washed with pentane and dried at 65 °C/2 Torr for 7 days to give (aS,7 1 1 /?)-(la) HCI (168 mg) as a yellowish solid.

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITAT DE BARCELONA - WO2014/206877, 2014, A1 Location in patent: Page/Page column 20

34
(+)-(7R,11R)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptan-1-amine [ No CAS ]
[ 541-41-3 ]
[ 102849-49-0 ]
(2S,7‴R,11‴R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: chloroformic acid ethyl ester; (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-(7R,11R)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptan-1-amine In dichloromethane at 20℃; for 72h;	9 Example 9: Preparation of (+)-(αS,7R,11R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide (αS,7R,11R)-(Ia) Example 9 Preparation of (+)-(αS,7R,11R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide (αS,7R,11R)-(Ia) A solution of (S)-2-(2-oxopyrrolidin-1-yl)butanoic acid (IIa) (99 mg, 0.58 mmol) in anhyd. CH2Cl2 (6 mL) was cooled to 0 °C with an ice bath, and treated dropwise with anhyd. Et3N (0.16 mL, 117 mg, 1.16 mmol) and ethyl chloroformate (0.05 mL, 62.8 mg, 0.58 mmol). The resulting mixture was stirred at 0 °C for 30 min and treated with a solution of amine (+)-(7R,11R)-(IIIa) (230 mg, 0.58 mmol) in anhyd. CH2Cl2 (5 mL). The reaction mixture was stirred at room temperature for 3 days and treated with 10% aq Na2CO3 (40 mL). The phases were separated and the aqueous phase was further extracted with CH2Cl2 (3 x 30 mL). The combined organic extracts were dried with anhyd. Na2SO4, filtered, and evaporated under reduced pressure to give a crude product (343 mg), which was subjected to column chromatography [40-60 µm silica gel (10 g), CH2Cl2/MeOH/50% aq NH4OH mixtures]. On elution with CH2Cl2/MeOH/50% aq NH4OH 99.95:0.05:0.2, the compound of the title (176 mg, 56% yield) was isolated as a yellowish solid. The isolated compound of the title was transformed into the corresponding hydrochloride as follows: A solution of the free base (176 mg, 0.32 mmol) in CH2Cl2 (15 mL) was filtered through a 0.2 µm NYL filter and treated with a 0.53 N methanolic solution of HCl (2.7 mL, 1.43 mmol). The solution was concentrated in vacuo to dryness and the solid residue was washed with pentane and dried at 65 °C/2 Torr for 7 days to give (αS,7R,11R)-(Ia)•HCl (168 mg) as a yellowish solid. Characterization: (αS,7R,11R)-(Ia): Rf = 0.70 (CH2Cl2/MeOH/50% aq NH4OH 9:1:0.05). (αS,7R,11R)-(Ia)•HCl: mp 102-105 °C (CH2Cl2/MeOH 85:15); [α]20D = +152 (c = 0.48, MeOH); IR (KBr) ν: 3500-2500 (max at 3256, 3055, 2925, 2860, 2796, N-H,+N-H, and C-H st), 1657, 1649, 1630, 1581, 1565, 1514 (C=O, ar-C-C and ar-C-N st) cm-1; HRMS (ESI) calcd for (C32H4335ClN4O2 + H+) 551.3147, found 551.3138. Elemental analysis, calcd for (C32H43ClN4O2•HCl•0.5H2O) C 64.42, H 7.60, N 9.39, Cl 11.88; found C 64.86, H 7.98, N 8.64, Cl 11.00.

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITAT DE BARCELONA - EP2818467, 2014, A1 Location in patent: Paragraph 0080

35
(+)-(7R,11R)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptane-1-amine [ No CAS ]
[ 102849-49-0 ]
(2S,7‴R,11‴R)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (+)-(7R,11R)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptane-1-amine In dichloromethane at 0 - 20℃; for 72h;

Reference： [1]Sola, Irene; Aso, Ester; Frattini, Daniela; López-González, Irene; Espargaró, Alba; Sabaté, Raimon; Di Pietro, Ornella; Luque, F. Javier; Clos, M. Victòria; Ferrer, Isidro; Muñoz-Torrero, Diego [Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6018 - 6032]

36
[ 249290-18-4 ]
[ 102849-49-0 ]
(-)-(αS)-N-{7-[(1,2,3,4-tetrahydroacridin-9-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine; chloroformic acid ethyl ester / dichloromethane / 0.5 h / 0 °C 1.2: 72 h / 0 - 20 °C 2.1: hydrogenchloride / methanol; dichloromethane

Reference： [1]Sola, Irene; Aso, Ester; Frattini, Daniela; López-González, Irene; Espargaró, Alba; Sabaté, Raimon; Di Pietro, Ornella; Luque, F. Javier; Clos, M. Victòria; Ferrer, Isidro; Muñoz-Torrero, Diego [Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6018 - 6032]

37
[ 249290-18-4 ]
[ 102849-49-0 ]
(-)-(αS)-N-{7-[(1,2,3,4-tetrahydroacridin-9-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: N-(7-aminoheptyl)-1,2,3,4-tetrahydroacridin-9-amine In dichloromethane at 0 - 20℃; for 72h;

Reference： [1]Sola, Irene; Aso, Ester; Frattini, Daniela; López-González, Irene; Espargaró, Alba; Sabaté, Raimon; Di Pietro, Ornella; Luque, F. Javier; Clos, M. Victòria; Ferrer, Isidro; Muñoz-Torrero, Diego [Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6018 - 6032]

38
(-)-(7S,11S)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptane-1-amine [ No CAS ]
[ 102849-49-0 ]
(2S,7‴S,11‴S)-N-{7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptyl}-2-(2-oxopyrrolidin-1-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30 mg	Stage #1: (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (-)-(7S,11S)-7-[(3-chloro-6,7,10,11-tetrahydro-9-methyl-7,11-methanocycloocta[b]quinolin-12-yl)amino]heptane-1-amine In dichloromethane at 0 - 20℃; for 72h;

Reference： [1]Sola, Irene; Aso, Ester; Frattini, Daniela; López-González, Irene; Espargaró, Alba; Sabaté, Raimon; Di Pietro, Ornella; Luque, F. Javier; Clos, M. Victòria; Ferrer, Isidro; Muñoz-Torrero, Diego [Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6018 - 6032]

39
[ 102849-49-0 ]
C₁₁H₁₇ClN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / water; tetrahydrofuran / 12.5 h / 0 - 20 °C 2: lithium tert-butoxide / dichloromethane; acetonitrile; hexane / 0.67 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: CELLIXBIO PRIVATE LTD - US9290486, 2016, B1

40
[ 102849-49-0 ]
C₁₉H₃₀N₂O₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / water; tetrahydrofuran / 12.5 h / 0 - 20 °C 2: lithium tert-butoxide / dichloromethane; acetonitrile; hexane / 0.67 h / 0 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 12.67 h / -10 - 20 °C

Reference： [1]Current Patent Assignee: CELLIXBIO PRIVATE LTD - US9290486, 2016, B1

41
[ 102849-49-0 ]
[(5Z,8Z,11Z,14Z,17Z)-2-oxo-2-((S)-2-(2-oxopyrrolidin-1-yl)butanamido)ethyl-icosa-5,8,11,14,17-pentaenoate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / water; tetrahydrofuran / 12.5 h / 0 - 20 °C 2: toluene / 3.5 h / 20 - 80 °C / Inert atmosphere 3: potassium carbonate; sodium iodide / acetone / 18 h / 20 °C

Reference： [1]Current Patent Assignee: CELLIXBIO PRIVATE LTD - US9290486, 2016, B1

42
[ 102849-49-0 ]
[(4Z,7Z,10Z,13Z,16Z,19Z)-2-oxo-2-((S)-2-(2-oxopyrrolidin-1-yl)butanamido)ethyl-docosa-4,7,10,13,16,19-hexanoate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; chloroformic acid ethyl ester; ammonium hydroxide / water; tetrahydrofuran / 12.5 h / 0 - 20 °C 2: toluene / 3.5 h / 20 - 80 °C / Inert atmosphere 3: potassium carbonate; sodium iodide / acetone / 18 h / 20 °C

Reference： [1]Current Patent Assignee: CELLIXBIO PRIVATE LTD - US9290486, 2016, B1

43
C₁₀H₁₇NO [ No CAS ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
123 mg	With sodium periodate In tetrachloromethane; water; acetonitrile at 20℃; Inert atmosphere;

Reference： [1]Liniger, Marc; Liu, Yiyang; Stoltz, Brian M. [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13944 - 13949]

44
1-[(2E)-1-ethylpent-2-en-1-yl]pyrrolidin-2-one [ No CAS ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-[(2E)-1-ethylpent-2-en-1-yl]pyrrolidin-2-one With dimethylsulfide; ozone In dichloromethane at -78 - 20℃; Stage #2: With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene In water; <i>tert</i>-butyl alcohol at 20℃;

Reference： [1]Narczyk, Aleksandra; Mrozowicz, Michał; Stecko, Sebastian [Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2770 - 2775]

45
[ 64-17-5 ]
[ 102849-49-0 ]
(S)-2-(2-Oxo-pyrrolidin-1-yl)-butyric acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid at 60℃; for 7h;	1.4.5 Step 5: 21.1 g (S)-α-ethyl-2-oxo-1-pyrrolidine acetic acid is added with absolute ethanol (10 mL/g) and p-toluenesulfonic acid (0.1 eq), the temperature was raised to 60 ° C for 7 hours, and the solution was concentrated to dryness under vacuum at 50 ° C. Add ethyl acetate (10 mL / g), stir, and washed with water (2.5mL / g) twice, The organic phase was concentrated to dryness in vacuo at 50 ° C to give (S)-α-ethyl-2-oxo-1-pyrrolidine ethyl acetate as an oil.

Reference： [1]Current Patent Assignee: SHANDONG POLYTECHNIC COLLEGE - CN110590635, 2019, A Location in patent: Paragraph 0043; 0056-0058

46
[ 86815-10-3 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 3 h / 60 °C 2.1: triethylamine / toluene / 80 - 90 °C 3.1: sodium hydroxide; water / 0.5 h / 0 - 10 °C 3.2: pH 4 - 5

Reference： [1]Current Patent Assignee: SHANDONG POLYTECHNIC COLLEGE - CN110590635, 2019, A

47
[ 909566-58-1 ]
[ 103833-72-3 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
87.1%	With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; water In aq. buffer for 11h; Electrolysis; Overall yield = 92 percentSpectr.;

Reference： [1]Zhong, Xing; Hoque, Md Asmaul; Graaf, Matthew D.; Harper, Kaid C.; Wang, Fei; Genders, J. David; Stahl, Shannon S. [Organic Process Research and Development, 2021, vol. 25, # 12, p. 2601 - 2607]

48
[ 96-48-0 ]
[ 5856-62-2 ]
[ 102849-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-butanolide; (S)-2-aminobutan-1-ol Stage #2: With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; water In aq. buffer for 0.6h; Electrolysis;

Reference： [1]Zhong, Xing; Hoque, Md Asmaul; Graaf, Matthew D.; Harper, Kaid C.; Wang, Fei; Genders, J. David; Stahl, Shannon S. [Organic Process Research and Development, 2021, vol. 25, # 12, p. 2601 - 2607]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	102849-49-0	MDL No. :	MFCD08272027
Formula :	C₈H₁₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IODGAONBTQRGGG-LURJTMIESA-N
M.W :	171.19	Pubchem ID :	11607993
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.24
TPSA :	57.61 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.12 cm/s

Log Po/w (iLOGP) :	1.38
Log Po/w (XLOGP3) :	0.31
Log Po/w (WLOGP) :	0.09
Log Po/w (MLOGP) :	0.13
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	0.49

[ CAS No. 102849-49-0 ] {[proInfo.proName]}

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[ 102849-49-0 ] Synthesis Path-Downstream 1~48

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[ 102849-49-0 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-0.9
Solubility :	21.6 mg/ml ; 0.126 mol/l
Class :	Very soluble
Log S (Ali) :	-1.08
Solubility :	14.2 mg/ml ; 0.0827 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.42
Solubility :	64.6 mg/ml ; 0.378 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-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. 102849-49-0 ] {[proInfo.proName]}

Quality Control of [ 102849-49-0 ]

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[ 102849-49-0 ] Synthesis Path-Downstream 1~48

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Amino Acid Derivatives

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Related Functional Groups of
[ 102849-49-0 ]