83623-88-5

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-(phenylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-
• Synonyms: (2S,4S)-4-Phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;N-Boc-L-cis-4-phenylthioproline
• CAS NO: 83623-88-5
• Molecular Formula: C16H21NO4S
• Molecular Weight: 323.413
• Mol File: 83623-88-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 76 - 79.5 °C
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-(phenylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-(phenylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(83623-88-5)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-(phenylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-(83623-88-5)

Safety Data

• Hazardous Substances Data: 83623-88-5(Hazardous Substances Data)

Usage

Common Use

Chiral building block in organic synthesis

Type

b-Tetronic acid derivative

Structural Features

Contains a pyrrolidine ring and a phenylthio group

Stereochemistry

(2S,4S)configuration at the 2nd and 4th carbon atoms

Applications

a. Pharmaceutical research and drug development
b. Potential biological activity
c. Precursor for other complex molecules
d. Materials science
e. Chiral catalyst in asymmetric synthesis

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 81653-77-2 (S)-4-phenylthio-L-proline 
• 686766-49-4 (2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 

Downstream Products

• 105107-84-4 C₁₁H₁₃NO₂S*ClH 
• 83551-92-2 1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline 
• 113949-54-5 C₂₉H₄₀N₂O₅SSi 
• 113949-53-4 (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 113949-43-2 N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester 

Relevant articles and documents

PYRROLIDINE ANALOGUE FOR PREVENTING NEUROGENIC PAIN AND METHOD FOR PRODUCTION THEREOF

[Problems] To provide a pyrrolidine analogue having an inhibitory activity on the induction of allodynia, a method for producing the pyrrolidine analogue, and an agent for preventing a neurogenic pain. [Means for Solving the Problems] A pyrrolidine analog

Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

Analogues of captopril, enalaprilat, and the phosphinic acid [[hydroxy(4-phenylbutyl)phosphinyl]acetyl)-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.