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Usage

Uses

Used in Pharmaceutical Research and Development:
(R)-4-Acetylthio-2-pyrrolidinone is used as a building block for the synthesis of complex molecules in the pharmaceutical industry. Its unique structure and properties contribute to the development of new drugs, making it a crucial component in this field.
Used in Organic Synthesis:
In the field of organic chemistry, (R)-4-Acetylthio-2-pyrrolidinone is used as a versatile compound for the production of various organic compounds. Its acetylthio functional group allows for a wide range of reactions and applications in creating diverse chemical structures.
Used in Materials Science:
(R)-4-Acetylthio-2-pyrrolidinone may also have potential uses in the field of materials science, where its unique properties can be harnessed to develop new materials with specific characteristics.
Used as a Reagent in Chemical Reactions:
Additionally, (R)-4-Acetylthio-2-pyrrolidinone serves as a reagent in various chemical reactions, facilitating the synthesis of different compounds and contributing to the advancement of chemical research.

Upstream product

• 68108-18-9 (4S)-4-hydroxypyrrolidin-2-one 
• 507-09-5 tiolacetic acid 
• 10387-40-3 potassium thioacetate 
• 75-36-5 acetyl chloride 
• 1972-28-7 diethylazodicarboxylate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 157429-42-0 (R)-4-mercaptopyrrolidin-2-one 

Relevant academic research and scientific papers

Practical synthesis of (R)-4-mercaptopyrrolidine-2-thione from L- aspartic acid. Preparation of a novel orally active 1-β-methylcarbapenem, TA-949

A facile and economical synthesis of a novel orally active 1-β- methylcarbapenem, TA-949 (1), is described. The key process involves an efficient synthesis of the C-2 side chain (R)-4-mercaptopyrrolidine-2-thione 2 from L-aspartic acid and the construction of the 1-β-methylcarbapenem skeleton. The mercapto group of 2 with an R-configuration was formed via deaminative bromination of the amino group of L-aspartic acid β-methyl ester hydrochloride 12 followed by a complete S(N)2-type substitution with potassium benzenemethanethiolate. High-yield amination and cyclization of the chloride 15 to the pyrrolidin-2-one 16 was accomplished by a simple treatment with ammonia. Thiation of 16 and the Birch reduction of the resultant thiolactam 18 provided the C-2 side chain 2 in high yield with the asymmetric center retained as such. The side chain 2 was installed into the 1-β- methylcarbapenem skeleton either by coupling with the vinyl phosphate 5 or by the use of the counterattack strategy involving the Dieckmann-type cyclization of the thioester 8. Removal of the protective groups of the coupling product 6 followed by esterification provided TA-949 (1) in high yield.

Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone derivatives

Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((5)-2) and (R)4- acetylthio-2-pyrrolidinone (S), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)- 3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3- (1-ethoxy)ethoxy-4-hydroxybutyramide (14).

Process for preparing optically active 4-mercapto-2-pyrrolidone derivative and intermediate therefor

A process for preparing an optically active 4-mercapto-2-pyrrolidone derivative of the formula [I]: STR1 wherein R1 is a hydrogen atom or a protecting group and R2 is a hydrogen atom or a protecting group, which comprises subjecting

Crystalline carbapenem derivative

A storage stable form of the pivaloyloxymethyl ester of the carbapenem derivative known as (1R, 5S, 6S)-2-[(4R)-2-oxo-4-pyrrolidinylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid in crystalline form.

Process for preparing optically active 4-mercapto-2-pyrrolidone derivative and intermediate therefor

A process for preparing an optically active 4-mercapto-2-pyrrolidone derivative of the formula: STR1 wherein a group of the formula: --SR1 is a protected or unprotected mercapto group, and the group of the formula: =NR2 is a protecte

1-Methylcarbapenem derivatives and process for preparation thereof

1-Methylcarbapenem derivatives of the formula: STR1 wherein R1 is hydrogen atom or a hydroxy-protecting group, R2 is hydrogen atom or an ester residue, R3 is hydrogen atom or a lower alkyl group, or salts thereof, which ha