Process for the manufacture of 7,16-dioxa-2-aza-10-0-...

Details Process for the manufacture of 7,16-dioxa-2-aza-10-0-... Process for the manufacture of 7,16-dioxa-2-aza-10-0-...

C - Chemistry, Metallurgy

07

H

260/230.3

C07H 17/00 (2006.01) C07H 17/08 (2006.01)

Patent

CA 1231943

ABSTRACT OF THE DISCLOSURE 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-ethyl- 3,5,9,11,13,15-hexamethylbicyclo[11.2.1]-hexadeca-1(2)-ene-8-one, a semi- synthetic macrolide annibiotic of the erythromycin A series, by means of Beckmann rearrangement of erythromycin A oxime monohydrochloride or di- hydrochloride with aromatic sulfochlorides of the formula 4-R-C6H4SO2Cl, wherein R stands for C1-C3 alkyl, halogen, acylamino of the formula -NHCOR1, stands for C1-C3 alkyl, in the presence of bases, without preliminary isolation of erythromycin A oxime. There is also provided the preparation of the novel intermediate erythromycin A oxime dihydrochloride from erythromycin A with hydroxylamine hydrochloride.

459064

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