93589-29-8Relevant academic research and scientific papers
MONOCYCLIC BETA-LACTAMS AND PROCESS FOR THE PREPARATION THEREOF
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, (2008/06/13)
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.
Synthesis and Biological Activity of Substituted oxy>acetic Acids. A New Class of Heteroatom-Activated β-Lactam Antibiotics
Woulfe, Steven R.,Miller, Marvin J.
, p. 1447 - 1453 (2007/10/02)
The synthesis of substituted oxy>acetic acids (1) is described. 3--N-hydroxy-2-azetidinones (13a, b), prepared from serine and threonine, were alkylated with 2-(trimethylsilyl)ethyl bromoacetate
