428518-42-7

Basic information

• Product Name: (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid
• Synonyms: (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid;3-Pyrrolidinecarboxylic acid, 5-oxo-1-(phenylmethyl)-, (3S)-
• CAS NO: 428518-42-7
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.2365
• Mol File: 428518-42-7.mol

Chemical Properties

• Melting Point: 100 °C
• Boiling Point: 471.3°C at 760 mmHg
• Flash Point: 238.8°C
• Density: 1.314g/cm³
• Vapor Pressure: 1.09E-09mmHg at 25°C
• Refractive Index: 1.604
• PKA: 4.51±0.20(Predicted)
• CAS DataBase Reference: (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid(428518-42-7)
• EPA Substance Registry System: (3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid(428518-42-7)

Safety Data

• Hazardous Substances Data: 428518-42-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid is used as a potential pharmaceutical agent for its ability to form hydrogen bonds and interact with biological receptors. Its structural similarities to other compounds with antimicrobial properties suggest that it may have potential as an antibacterial or antifungal agent.
Used in Drug Development:
(3S)-1-benzyl-5-oxopyrrolidine-3-carboxylic acid is used in drug development for its potential to be further studied and developed into new pharmaceuticals. Its unique three-dimensional structure and functional group arrangement make it a promising candidate for the creation of novel therapeutic agents.

Upstream product

• 5733-86-8 1-benzyl-5-oxopyrrolidine-3-carboxylic acid 
• 100-46-9 benzylamine 
• 617-52-7 Dimethyl itakonate 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 

Downstream Products

• 1042903-94-5 C₃₇H₄₂F₂N₄O₆ 
• 428518-44-9 methyl (S)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylate 
• 216311-58-9 methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate 
• 216311-60-3 (3S)-pyrrolidine-3-carboxylic acid methyl ester 
• 110013-19-9 (S)-(-)-3-(hydroxymethyl)pyrrolidine 
• 78914-69-9 (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride 

Relevant articles and documents

Asymmetric Reduction of Lactam-Based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1-3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity

Resolution of racemic 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid with enantiopure (S)-phenylalanine N-benzylamide via diastereomeric salt formation

The resolution of racemic 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid 1, a potent chiral synthon with high pharmacological activity, was investigated with a variety of basic chiral resolving agents via diastereomeric salt formation. The findings in the optimization of resolution conditions aiming at an industrial-scale production revealed that (S)-phenylalanine benzylamide (S)-10 and 2-propanol containing ca. 4 mol % of water to (RS)-1 were the best conditions for obtaining enantiopure less-soluble diastereomeric salt, (S)-1/(S)-10/0.5H2O (81%, 98% de, E 79%). X-ray crystallographic analysis of the salt clearly revealed that water molecules play a key role in crystallizing the enantiopure salt crystals, while stabilizing the crystal structure via three types of hydrogen-bond network associated with water molecules in addition to usual acid-base hydrogen bond.

A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline

Enantiopure methyl esters of 1-alkyl-5-oxo-3-pyrrolidinecarboxylic acids were obtained by enzymatic resolution of the corresponding chiral racemic mixtures. A particularly favourable interaction, also supported by molecular mechanics calculations, was observed between the 1-benzyl derivative and α-chymotrypsin, for which the enantiomeric ratio, E, exceeded 200. The absolute configurations of the lactams were determined by means of CD spectroscopy. From the resulting enantiomerically pure (99% e.e.) (S)-(+)-1-benzyl-3-pyrrolidinecarboxylic acid and methyl (R)-(-)-1-benzyl-3-pyrrolidinecarboxylate, the methyl esters of (+) and (-)-β-proline were synthesised in 99% e.e. and 18 and 22% overall yield, respectively.