Ceftibuten:: Development of a commercial process based on cephalosporin C.: Part I.: Process for the manufacture of 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid 1(S)-oxide

The manufacture of low-cost, orally active cephalosporin drugs has, until now, been achieved using intermediates prepared by the ring expansion of penicillin sulfoxides rather than fermented cephalosporin C. This report describes the preparation of 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid 1(S)-oxide (8) from cephalosporin C broths. This new intermediate has been shown (see the following contributions) to be a superior starting material for the low-cost preparation of the orally active cephalosporin, Ceftibuten.