Ceftibuten: Development of a Commercial Process Based on Cephalosporin C. Part IV. Pilot-Plant Scale Electrochemical Reduction of 3-Acetoxymethyl-7(<i>R</i>)-glutaroylaminoceph-3-em-4-carboxylic Acid 1(<i>S</i>)-Oxide

Abstract

This contribution describes the operation of a pilot plant for the production of 3-exomethylene-7(R)-glutaroylaminocepham-4-carboxylic acid 1(S)-oxide (4a) by the electrochemical reduction of 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid 1(S)-oxide (3a). This conversion is a key step in a new process for the production of Ceftibuten (1). The scale-up of the electrochemical reduction was demonstrated using a commercial flow-cell. The use of a novel type of extended-area tin cathode, which had been shown on a laboratory scale to produce significant improvements in the process, was successfully implemented in an ICI FM21-SP commercial-scale electrochemical reactor.