One step process for production of dirithromycin

Details One step process for production of dirithromycin One step process for production of dirithromycin

1993-07-20

1996-11-26

Peselev, Elli

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 72, 536 74, C07H 100

Patent

active

055787134

ABSTRACT:
The disclosure relates to a new process for the synthesis of the macrolide antibiotic dirithromycin in crystalline form. The process is carried out in a single reaction vessel whereby an acetal dissolved in acetonitrile, in the presence of an acid catalyst, is hydrolyzed to the related hemiacetal which then reacts directly with erythromycylamine to form crystalline dirithromycin.

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Counter et al, Antimicrobial Agents and Chemotherapy, Jun. 1991, pp. 1116-1121.
Luger and Maier, Molecular structure of 9-deoxy-11-deoxy-9-11-(imino(2-(2-methoxyethoxy)ethylidene)oxy)-(9S)-eryth romycin, a new erythromycin derivative, Journal of Crystal and Molecular Structure, 9:329-338 (1979).
Dirithromycin, Drugs of the Future 14:112-115 (1989).
Firl et al., Epimerization of erythromycin derivatives, Journal of Antibiotics 43:1271-77 (1990).
Counter, et al., "Synthesis and Antimicrobial Evaluation of Dirithromycin", Antimicrobial Agents and Chemotherapy, vol. 35, No. 6, pp. 1116-1126, Jun., 1991.

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