184759-58-8

Basic information

• Product Name: (S)-4-MERCAPTO-2-PYRROLIDINONE
• Synonyms: 2-PYRROLIDINONE, 4-MERCAPTO-, (S);(S)-4-MERCAPTO-2-PYRROLIDINONE;2-Pyrrolidinone,4-mercapto-,(S)-(9CI)
• CAS NO: 184759-58-8
• Molecular Formula: C4H7NOS
• Molecular Weight: 117.17
• Product Categories: THIOL
• Mol File: 184759-58-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-4-MERCAPTO-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-MERCAPTO-2-PYRROLIDINONE(184759-58-8)
• EPA Substance Registry System: (S)-4-MERCAPTO-2-PYRROLIDINONE(184759-58-8)

Safety Data

• Hazardous Substances Data: 184759-58-8(Hazardous Substances Data)

Usage

Description

(S)-4-Mercapto-2-pyrrolidinone, also known as thiazolidine-2-thione, is a chemical compound with the molecular formula C4H7NOS. It belongs to the class of pyrrolidinone derivatives and is characterized by a five-membered ring containing a sulfur atom, a nitrogen atom, and a carbonyl group. (S)-4-MERCAPTO-2-PYRROLIDINONE is known for its ability to undergo a variety of chemical reactions, making it a versatile building block in the synthesis of various pharmaceuticals and organic compounds. Furthermore, (S)-4-mercapto-2-pyrrolidinone exhibits antioxidant and anti-inflammatory properties, which contribute to its potential utility in the development of therapeutic agents.

Uses

Used in Pharmaceutical Synthesis:
(S)-4-Mercapto-2-pyrrolidinone is used as a precursor in the pharmaceutical industry for the synthesis of various drugs and organic compounds. Its unique chemical structure allows it to participate in a wide range of reactions, making it a valuable component in the development of new medications.
Used in Antioxidant and Anti-inflammatory Applications:
(S)-4-Mercapto-2-pyrrolidinone is used as an antioxidant and anti-inflammatory agent in the development of therapeutic agents. Its ability to counteract oxidative stress and reduce inflammation makes it a promising candidate for the treatment of various conditions, including those involving chronic inflammation or oxidative damage.
Used in Chemical Research:
In the field of chemical research, (S)-4-mercapto-2-pyrrolidinone serves as a valuable compound for studying various reaction mechanisms and exploring new synthetic pathways. Its reactivity and structural features make it an attractive subject for research aimed at discovering novel chemical processes and applications.

Upstream product

• 108309-78-0 4-(p-methoxybenzylthio)-2-pyrrolidone 
• 142705-97-3 (R)-4-acetylthio-2-oxopyrrolidine 

Relevant articles and documents

Trials for the synthesis of (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD)

Several trials were made for the syntheses of (S)-4-hydroxy-pyrrolidin- 2-one ((S)-HPD) and (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD), a substituent at the 2-position of the orally active carbapenem antibiotic CS-834. The latter was synthesized from prochiral dimethyl or diethyl 3-p- methoxybenzylthioglutarate using pig liver esterase technology to give monoester with an optical purity of 51-71% e.e. as a key intermediate.

2-(heterocyclylthio)carbapenem derivatives, their preparation and their use as antibiotics

Compounds of formula (I): STR1 in which Ra is a group of formula (II): STR2 or a group of formula (III): STR3 (where one of R' is a bond to the remainder of the compound, one more of R' is R2 and the others of R' are all hydrogen), R1 is hydrogen or methyl, R2 is hydrogen, optionally substiuted alkyl, halogen, hydroxy, alkoxy, amino, alkanoylamino, alkanoyloxy, alkanoyl, carboxy, alkoxycarbonyl, cyano, --S(O)j R9 (where j is 0, 1 or 2 and R9 is alkyl), or --CONR6 R7 (which is optionally substituted carbamoyl or heterocyclyl-carbonyl), R2a is hydrogen, alkyl or alkanoyl, --NR3 R4 is optionally substituted amino or heterocyclic, and --COOR5 is carboxy, --COO-, --COOMx (where M is a cation and x is the reciprocal of the valence of the cation M) or protected carboxy and, where --COOR5 is carboxy, --COOMx or protected carboxy, the compound of formula (I) also contains an anion; l, m and n are independently 0, 1, 2 or 3, provided that (m+n) is an integer from 2 to 6; p is 0, 1 or 2; Y is a single bond, oxygen, sulfur or R8 N8 is hydrogen, alkyl or alkanoyl) and pharmaceutically acceptable salts and esters thereof are potentially valuable antibiotics.