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.