94944-06-6

Upstream product

• 5883-82-9 2-((4-methoxyphenyl)amino)-1-phenylethanone 
• 86561-72-0 (2R,3R)-2,3-epoxybutanoic acid 
• 113318-74-4 (2R,3R)-epoxybutanoic acid chloride 
• 104401-69-6 (2S,3R)-N-(4-methoxyphenyl)-N-(benzoylmethyl)-2-bromo-3-hydroxybutyramide 
• 70-11-1 α-bromoacetophenone 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 94944-07-7 (3S,4S,1'R) N-p-methoxyphenyl-3-(1'-hydroxyethyl)-4-benzoylazetidin-2-one 
• 94944-08-8 (3S,4S)-4-Benzoyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-azetidin-2-one 
• 94944-09-9 [3S-[3α(S*),4β]]-4-benzoyl-3-[1-[[[(1,1-dimethyl-ethyl)dimethyl]silyl]oxy]ethyl]-2-azetidinone 

Relevant academic research and scientific papers

A (2 R, 3 R) - N - (benzoyl) methyl - N - 4 - methoxyphenyl - 2, 3 - scale inhibitor amide preparation method (by machine translation)

The invention relates to a preparation method of (2R, 3R)-N-(benzoyl)methyl-N-4-methoxyphenyl-2, 3-epoxy butyramide. The method includes: dissolving (2R, 3R)-epoxy butyric acid in an organic solvent, then adding an acid-binding agent and 2-(4-methoxypheny

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.

Process for the preparation of 2,3-epoxyamides

A process for the preparation of a 2,3-epoxyamide of the formula STR1 in which R1 represents hydrogen or straight-chain or branched C1 -C8 -alkyl, which may be substituted by phenyl or halogen, or represents C3