87791-64-8

Upstream product

• 63591-85-5 phenylacetic acid N-hydroxysuccinimide ester 
• 80582-04-3 (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 102652-77-7 O-acetyl N-(benzyloxycarbonyl)-L-threoninehydroxamate 
• 93589-31-2 N-hydroxy-4(S)-methyl-3(S)-<(benzyloxy)formamido>-2-azetidinone 
• 87791-63-7 Trifluoro-acetic acid; compound with (S)-3-amino-4-methyl-azetidin-2-one 
• 103-80-0 phenylacetyl chloride 
• 112026-51-4 ethyl 3-(p-anisidino)-2-(phenylacetylamino)butanoate 
• 112026-50-3 ethyl 3-(p-anisidino)-2-(phenylacetylamino)but-2-enoate 
• 92246-33-8 ethyl 2-(phenylacetylamino)acetoacetate 
• 112026-52-5 cis-N-(4-methoxyphenyl)-4-methyl-3-(phenylacetylamino)azetidin-2-one 

Downstream Products

• 87791-65-9 4-methyl-3-phenylacetamido-1-dibenzylphosphoryl-2-azetidinone 
• 87791-66-0 4-methyl-3-phenylacetamido-1-phosphoryl-2-azetidinone 
• 80082-64-0 (2R,3S)-2-Methyl-4-oxo-3-phenylacetylamino-azetidine-1-sulfonatetetrabutyl-ammonium; 

Relevant academic research and scientific papers

Stereoselective synthesis of cis-4-(substituted) monobactams from ethyl acetoacetate

The stereoselective synthesis of cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (25) from ethyl acetoacetate is described. Nitrosation of this compound and reduction of the resulting oxime gave the corresponding amine, which after treatment with different acyl halides, yielded the acylamino derivatives (6)-(8). Condensation with p-anisidine gave the enamines (12)-(14), which were then reduced to the β-amino acid esters (15)-(17). Stereoselective cyclization with Grignard reagents as base, and appropriate deprotection and sulphonation of the resulting β-lactams (18)-(20), led to the title compounds.

The Synthesis of Substituted thio>acetic Acids

The synthesis of substituted thio>acetic acids (6, thiamazins) is described.Various substituted 3(S)-(acylamino)-2-azetidinones were sulfenylated with tert-butyl (phtalimidothio)acetate.Deprotection of the tert-butyl ester with trifluoroacetic acid provided the title compounds.In sharp contrast to their oxygen analogues (oxamazins), the thiamazins were devoid of biological activity.