82933-31-1

Upstream product

• 103-80-0 phenylacetyl chloride 
• 82933-32-2 N-(phenylacetyl)-L-threonine O-benzylhydroxyamide 
• 2798-50-7 (2S,3R)-3-hydroxy-2-(2-phenylacetamido)butanoic acid 
• 82933-33-3 N-((2S,3S)-1-Benzyloxy-2-methyl-4-oxo-azetidin-3-yl)-2-phenyl-acetamide 

Downstream Products

• 82933-35-5 Sulfuric acid mono-((2S,3S)-2-methyl-4-oxo-3-phenylacetylamino-azetidin-1-yl) ester; compound with pyridine 
• 82951-08-4 (2S,3S)-3-Hydroxyamino-2-phenylacetylamino-butyric acid 
• 93589-29-8 benzyl <<4(S)-methyl-3(S)-(phenylacetamido)-2-oxo-1-azetidinyl>oxy>acetate 
• 93712-27-7 <<4(S)-methyl-3(S)-(phenylacetamido)-2-oxo-1-azetidinyl>oxy>acetic acid 

Relevant academic research and scientific papers

MONOCYCLIC BETA-LACTAMS AND PROCESS FOR THE PREPARATION THEREOF

Monocyclic beta-lactam compounds represented by the formula STR1 wherein R 1 is H, NH 2, acylamino, C 1 -C 4 alkyl, etc.; R 2 is e.g. C 1 -C 4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R 3 is hydrogen, benzyl, substituted benzyl, pivaloyl, --SO 3 M, or --P(C-O)(OM')2; are obtained by the cyclization of an O-substituted hydroxamate of a beta-substituted alkylcarboxylic acid. For example, alpha-ethylmalic acid monobenzyl ester is reacted with O-benzylhydroxylamine to form the O-benzylhydroxamate of the free carboxy group, and the hydroxamate is cyclized with diethyl diazodicarboxylate and triphenylphosphine to form the beta-lactam of the above formula wherein R 1 is ethyl, R 2 is benzyloxycarbonyl and R 3 is benzyl. The beta-lactam compounds are useful intermediates for preparing beta-lactamase inhibitors and monocyclic beta-lactam antibiotics and, when R 3 is --SO 3 M or -P(C-O)(OM')2 the compounds and salts thereof are antibacterial agents.

O-sulfated β-lactam hydroxamic acids and intermediates

Antibacterial activity is exhibited by β-lactams having a sulfate substituent in the 1-position and an acylamino substituent in the 3-position.