Issue 0, 1966

Cephalosporanic acids. Part IV. 7-Acylamidoceph-2-em-4-carboxylic acids

Abstract

The combined action of bases and acid anhydrides on 7-acylamidocephalosporanic acids, and the action of bases on their esters, set up equilibria in which the corresponding Δ2-isomers predominate. The isomerisation represents a prototropic shift probably favoured by the sulphur atom in the dihydrothiazine ring. The acetoxy-group in the Δ2-compounds can be replaced by nucleophiles.

Treatment of methyl 3-acetoxymethyl-7β-phenylacetamidoceph-3-em-4-carboxylate 1ξ-oxide with a base results in decarboxylation. Attempts to prepare 7β-phenylacetamidoceph-2-em-4ξ-carboxylic acid 1ξ-oxide resulted in formation of its Δ3-isomer and some carbon dioxide.

Article information

Article type
Paper

J. Chem. Soc. C, 1966, 1142-1151

Cephalosporanic acids. Part IV. 7-Acylamidoceph-2-em-4-carboxylic acids

J. D. Cocker, S. Eardley, G. I. Gregory, M. E. Hall and A. G. Long, J. Chem. Soc. C, 1966, 1142 DOI: 10.1039/J39660001142

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