ethyl (2S)-5-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: ethyl (2S)-5-oxopyrrolidine-2-carboxylate
• CAS No.: 7149-65-7
• Molecular Formula: C7H11 N O3
• Molecular Weight: 157.169
• Hs Code.: 2933790090
• European Community (EC) Number: 230-480-9
• UNII: 1PS59ES316
• DSSTox Substance ID: DTXSID201303392
• Nikkaji Number: J227.409D
• Pharos Ligand ID: ZSKNGT2CXW3C
• ChEMBL ID: CHEMBL4229168
• Mol file: 7149-65-7.mol

Synonyms:7149-65-7;L-Pyroglutamic acid ethyl ester;Ethyl L-pyroglutamate;ethyl (2S)-5-oxopyrrolidine-2-carboxylate;(S)-ethyl 5-oxopyrrolidine-2-carboxylate;Ethyl pidolate;Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate;H-Pyr-OEt;(S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone;Ethyl 5-oxo-L-prolinate;Ethyl pyroglutamate;(+)-L-Pyroglutamic acid ethyl ester;MFCD00064497;UNII-1PS59ES316;CHEMBL4229168;1PS59ES316;EINECS 230-480-9;NSC-72279;NSC-166529;NSC 72279;NSC 166529;ETHYL PCA;VAMACTIVE 47;ETHYL PCA [INCI];pyroglutamic acid ethyl ester;SCHEMBL905284;ETHYL (S)-PYROGLUTAMATE;L-Proline, 5-oxo-, ethyl ester;QYJOOVQLTTVTJY-YFKPBYRVSA-N;DTXSID201303392;AC-708;BDBM50460039;Ethyl 5-oxo-2-pyrrolidinecarboxylate;AKOS005259612;AKOS015909837;CS-W020688;DS-1658;ethyl (S)-2-pyrrolidone-5-carboxylate;BP-12288;Ethyl (S)-2-oxopyrolidine-5-carboxylate.;Ethyl (S)-5-oxopyrrolidine-2-carboxylate;ETHYL L-2-PYRROLIDONE-5-CARBOXYLATE;PROLINE, 5-OXO-, ETHYL ESTER, L-;A9360;AM20100678;ethyl (s)-(+)-2-pyrrolidinone-5-carboxylate;EN300-185981;ETHYL L-2-OXO-5-PYRROLIDINECARBOXYLATE;AQ-405/40679537;(S)-(+)-ETHYL 2-PYRROLIDONE-5-CARBOXYLATE;Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate, 98%;Q-101629;(2S)-5-Oxopyrrolidine-2-carboxylic acid ethyl ester;(S)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester;Q27252722;L-Pyroglutamic acid ethyl ester, puriss., >=98.5% (sum of enantiomers, HPLC)

Chemical Property of ethyl (2S)-5-oxopyrrolidine-2-carboxylate

Chemical Property:

• Appearance/Colour: Colorless or yellowish oily liquid
• Melting Point: 47-51 ºC
• Refractive Index: 1.4310 (estimate)
• Boiling Point: 176 ºC (12 mmHg)
• PKA: 14.78±0.40(Predicted)
• Flash Point: 142.9 °C
• PSA: 55.40000
• Density: 1.161 g/cm₃
• LogP: 0.15690
• Storage Temp.: 0-6°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 157.07389321
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

min 98% ^*data from raw suppliers

(S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCC(=O)N1
• Isomeric SMILES: CCOC(=O)[C@@H]1CCC(=O)N1
• Uses: (S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone (cas# 7149-65-7) is a compound useful in organic synthesis.

Technology Process of ethyl (2S)-5-oxopyrrolidine-2-carboxylate

There total 16 articles about ethyl (2S)-5-oxopyrrolidine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethanol (64-17-5) + (S,S)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,6,8,12-tetrone (14842-41-2) → ethyl (S)-pyroglutamate (7149-65-7)

Guidance literature:

With potassium cyanide; for 4h;

DOI:10.1021/jo0160928

Reference yield: 99.0%

ethanol (64-17-5) + L-Pyroglutamic acid (98-79-3) → ethyl (S)-pyroglutamate (7149-65-7)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1002/anie.201001739

Reference yield: 95.0%

ethanol (64-17-5) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → ethyl (S)-pyroglutamate (7149-65-7)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1055/s-2006-939046

upstream raw materials:

ethanol

L-glutamic acid

L-glutamic acid diethyl ester

diethyl-L-glutamate hydrochloride

Downstream raw materials:

L-1-(chlorocarbonyl)proline ethyl ester

1-(3-phenyl-2-propenyl)-5-carboethoxy-2-pyrrolidinone

1-(2-cyclohexenyl)-5-carboethoxy-2-pyrrolidinone

ethanol

Refernces

• 1、 -. "IMPROVED PROCESS FOR THE PREPARATION OF (2S)-N-{(1S)-1-(2-CHLOROPHENYL)-2-[(3,3-DIFLUOROCYCLOBUTYL)-AMINO]-2-OXOETHYL}-1-(4-CYANOPYRIDIN-2-YL)-N-(5-FLUOROPYRIDIN-3-YL)-5-OXOPYRROLIDINE-2-CARBOXAMIDE". Page/Page column 29-30. . Retrieved 2021/04/30.
• 2、 Nirogi, Ramakrishna,Mohammed, Abdul Rasheed,Shinde, Anil K.,Ravella, Srinivasa Rao,Bogaraju, Narsimha,Subramanian, Ramkumar,Mekala, Venkat Reddy,Palacharla, Raghava Choudary,Muddana, Nageswararao,Thentu, Jagadeesh Babu,Bhyrapuneni, Gopinadh,Abraham, Renny,Jasti, Venkat. "Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression". . p. 2833 - 2853. Retrieved 2020/03/05.