CLEAVAGE AND SOME MODIFICATIONS OF THE 7-AMIDE GROUP OF THE CEPHAMYCINS

Article abstract of DOI:10.1016/0040-4020(80)80149-9

The cleavage and some modifications of the 7-amide group of cephamycins are described.Cephamycin derivatives 16b, c which were synthesized from the naturally occuring cephamycin C (16a) were converted to the corresponding oxamic acid derivatives 17a, e respectively by the reaction with oxalyl chloride and successive treatment with water.The reaction of the oxamic acid 17a with diphenylcarbodiimide gave 7-aminocephamycinoic acid (7-ACMA) benzhydryl ester (21a) which was further converted to cefoxitin (21c).These compounds 17a, b, c, d, e, f thus obtained from cephamycin C appear to be favorable intermediates for the syntheses of cephamycin analogues such as cefmetazole (28c).