141628-82-2

Basic information

• Product Name: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester
• Synonyms: TA-949
• CAS NO: 141628-82-2
• Molecular Formula: C₁₉H₂₆N₂O₆S₂
• Molecular Weight: 442.55687
• Mol File: 141628-82-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester(141628-82-2)
• EPA Substance Registry System: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester(141628-82-2)

Safety Data

• Hazardous Substances Data: 141628-82-2(Hazardous Substances Data)

Upstream product

• 153976-19-3 S-[(R)-pyrrolidine-2-thion-4-yl]-(R)-2-{(3S,4S)-1-allyloxycarbonylmethyl-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl}thiopropionate 
• 153471-14-8 allyl (4R,5R,6S)-6-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-3-[(R)-pyrrolidine-2-thion-4-ylthio]-4-methyl-7-oxo-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 153471-13-7 allyl (4R,5R,6S)-6-[(R)-1-(hydroxy)ethyl]-3-[(R)-pyrrolidine-2-thion-4-ylthio]-4-methyl-7-oxo-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 63379-62-4 isobutyryloxymethyl iodide 

Relevant articles and documents

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.