Process for the manufacture of 7,16-dioxa-2-aza-10-0-cladinosyl-12-0-desosaminyl-4,5-dihydroxy-6-ethyl-3,5,9,11,13,15-hexamethyl-bicyclo(11.2.1)-hexadeca-1(2)-ene-8-one and novel intermediate used in this process.

摘要

The invention relates to a new process for the manufacture of 7,16-dioxa-2-aza-10-0-cladinosyl-12-0-desosaminyl-4,5-dihydroxy-6-ethy l-3,5,9,11,13,15-hexamethyl-bicyclo[11.2.1]- hexadeca-1(2)-ene-8-one, a semisynthetic macrolide antibiotic of the erythromycin A series, by means of Beckmann rearrangement of erythromycin A oxime monohydrochloride or dihydrochloride with aromatic sulfochlorides of the formula 4-R-C6H4SO2Cl, wherein R stands for C1-C3 alkyl, halogen, acylamino of the formula -NHCOR1, wherein R1 stands for C1-C3 alkyl, in the presence of bases, without preliminary isolation of erythromycin A oxime. There is also provided a novel imtermediate erythromycin A oxime dihydrochloride and the preparation thereof from erythromycin A with hydroxylamine hydrochloride.