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1-Acetoxyethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3- [(Z)-1-propenyl]-3-cephem-4-carboxylate (BMY-28271) is an ester-type prodrug of cephalosporin for oral use. Methods suitable for large scale preparation were investigated. The yield was improved by esterification of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]cep hem-4-carboxylic acid (11) followed by removal of the trityl group and, in addition, column chromatographic purification at each step was eliminated by optimization of the reaction conditions.

journal of antibiotics

Improved synthesis of an ester-type prodrug, 1-acetoxyethyl 7-((Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-((Z)-1-propenyl)-3-cephem-4-carboxylate (BMY-28271).