(2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid

Base Information

• Chemical Name: (2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid
• CAS No.: 102849-49-0
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.196
• European Community (EC) Number: 600-362-5
• UNII: S19061909R
• ChEMBL ID: CHEMBL1287
• DSSTox Substance ID: DTXSID00145541
• Nikkaji Number: J1.061.198I
• Wikidata: Q27288442
• Mol file: 102849-49-0.mol

Synonyms:102849-49-0;(2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid;(S)-2-(2-oxopyrrolidin-1-yl)butanoic acid;Levetiracetam Carboxylic Acid;Levetiracetam acid, (-)-;2-(2-Oxopyrrolidin-1-yl)butanoic acid, (2S)-;2-Pyrrolidinone-N-butyric acid;UCB-L 057;S19061909R;(S)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID;(s)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid;(S)-Levetiracetam acid;1-Pyrrolidineacetic acid, alpha-ethyl-2-oxo-, (alphaS)-;MFCD08272027;(2S)-2-(2-Oxopyrrolidin-1-yl)butanoicacid;UNII-S19061909R;CHEMBL1287;Levetiracetam impurity, levetiracetam acid- [USP];SCHEMBL1877216;DTXSID00145541;CHEBI:143418;IODGAONBTQRGGG-LURJTMIESA-N;AKOS006285768;AKOS015841982;AC-1460;AS-64846;(S)-2-(2-oxopyrrolidin-1-yl)butanoicacid;(s)-2-(2-oxopyrrolidin-1-yl) butyric acid;(2S)-2-(2-oxo-1-pyrrolidinyl)butanoic acid;(S)-alpha-ethyl-2-oxo pyrrolidine acetic acid;EN300-7808596;Levetiracetam carboxylic acid metabolite (L057);A800630;J-501010;Q27288442;(s)-2-(2-oxopyrrolidin-1-yl)butanoic acid, C~8~H~13~NO~3~;1-Pyrrolidineacetic acid, .alpha.-ethyl-2-oxo-, (.alpha.S)-;LEVETIRACETAM IMPURITY, LEVETIRACETAM ACID- [USP IMPURITY]

Chemical Property of (2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 118-121°C
• Refractive Index: 1.517
• Boiling Point: 370.975 °C at 760 mmHg
• PKA: 3.76±0.10(Predicted)
• Flash Point: 178.16 °C
• PSA: 57.61000
• Density: 1.227 g/cm³
• LogP: 0.40990
• Storage Temp.: -20°C Freezer
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.08954328
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

LevetiracetamCarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)O)N1CCCC1=O
• Isomeric SMILES: CC[C@@H](C(=O)O)N1CCCC1=O
• Uses: Levetiracetam intermediate.

Technology Process of (2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid

There total 16 articles about (2S)-2-(2-Oxopyrrolidin-1-yl)butanoic acid 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: 94.5%

→ (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid (102849-49-0)

Guidance literature:

Reference yield: 90.0%

(S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt (102916-46-1) → (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid (102849-49-0)

Guidance literature:

With hydrogenchloride; In water;

Reference yield: 90.0%

1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one (909566-58-1) → (2S)-2-(2-oxopyrrolidin-1-yl)butanoic acid (102849-49-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 25 ℃; for 6h; pH=6.8;

DOI:10.1016/j.tetlet.2006.07.061

upstream raw materials:

(αS,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate

2-pyrrolidinon

(2R)-2-bromobutanoic acid

1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one

Downstream raw materials:

(S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate

levetiracetam

Refernces

• 1、 -. "Preparation method of levetiracetam and intermediates thereof". . . Retrieved 2020/01/08.
• 2、 Liniger, Marc,Liu, Yiyang,Stoltz, Brian M.. "Sequential ruthenium catalysis for olefin isomerization and oxidation: Application to the synthesis of unusual amino acids". supporting information. p. 13944 - 13949. Retrieved 2017/11/06.