691357-67-2

Basic information

• Product Name: (2R,3R)-N-(2-cyclopropyl-2-oxoethyl)-N-diphenylmethyl-2,3-epoxybutanamide
• Synonyms: (2R,3R)-N-(2-cyclopropyl-2-oxoethyl)-N-diphenylmethyl-2,3-epoxybutanamide
• CAS NO: 691357-67-2
• Molecular Weight: 349.43
• Mol File: 691357-67-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R)-N-(2-cyclopropyl-2-oxoethyl)-N-diphenylmethyl-2,3-epoxybutanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-N-(2-cyclopropyl-2-oxoethyl)-N-diphenylmethyl-2,3-epoxybutanamide(691357-67-2)
• EPA Substance Registry System: (2R,3R)-N-(2-cyclopropyl-2-oxoethyl)-N-diphenylmethyl-2,3-epoxybutanamide(691357-67-2)

Safety Data

• Hazardous Substances Data: 691357-67-2(Hazardous Substances Data)

Upstream product

• 91-00-9 Benzhydrylamine 
• 69267-75-0 2-bromo-1-cyclopropylethan-1-one 
• 765-43-5 Cyclopropyl methyl ketone 
• 113318-74-4 (2R,3R)-epoxybutanoic acid chloride 
• 691357-65-0 1-cyclopropyl-2-[(diphenylmethyl)amino]ethanone 

Downstream Products

• 691357-70-7 (3S,4S)-4-(cyclopropyl-oxomethyl)-N-diphenylmethyl-3-[(1R)-1-hydroxyethyl]azetidin-2-one 
• 691357-81-0 (3S,4S)-4-Cyclopropanecarbonyl-1-(hydroxy-diphenyl-methyl)-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 

Relevant articles and documents

Synthesis of (1′R,3S,4S)-3-[1′-(tert-butyldimethylsilyloxy) ethyl]-4-(cyclopropylcarbonyloxy)azetidin-2-one

The novel carbapenem precursor 1e has been synthesized from L-threonine, cyclopropyl methyl ketone and benzhydrylamine (for the introduction of the azetidinone N-protecting group). Two independently prepared building blocks - sodium (2R,3R)-2,3-epoxybutyrate as a mixed salt with NaBr (2b) and N-(benzhydryl)aminomethyl cyclopropyl ketone (4e) - were coupled to give (2R,3R)-N-(benzhydryl)-N-(2-cyclopropyl-2-oxoethyl)-2,3-epoxybutyramide (8e). This key intermediate gave a regio- and stereoselective C3-C4 ring closure on LiHMDS treatment in THF at 0°C to yield (1′R,3S,4S)-4- cyclopropylcarbonyl-1-diphenylmethyl-3-(1-hydroxyethyl)azetidin-2-one (13e). N-Deprotection of 13e was performed by photochemical bromination and subsequent hydrolysis. The resulting (1′R,3S,4S)-4-(cyclopropylcarbonyl)-3-(1- hydroxyethyl)azetidin-2-one (23e) reacted in a Baeyer-Villiger oxidation with a total control of the regioselectivity (due to the poor migratory aptitude of the cyclopropyl group) to furnish (1′R,3S,4S)-3-(1-hydroxyethyl)-4- (cyclopropylcarbonyloxy)azetidin-2-one (24e), subsequent O-silylation achieving the total synthesis of 1e (title compound). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.