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Translactonization of erythromycin A during oximation: mixture analysis and reaction monitoring by NMR

✍ Scribed by Rajesh K. Grover; B. S. Joshi; S. Batra; Raja Roy; A. P. Bhaduri

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
172 KB
Volume
39
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Oximation of erythromycin A with hydroxylamine hydrochloride and sodium acetate in methanol led to the formation of pseudoerythromycin A enol ether with erythromycin A oxime as analysed by detailed two‐dimensional NMR spectroscopy in the mixture along with traces of 8,9‐anhydroerythromycin A 6,9‐hemiketal and erythromycin A 6,9:9,12‐spiroketal. The formation of the degraded products was established by performing in situ ^13^C NMR spectroscopy. The analysis suggests that pseudoerythromycin A enol ether is formed by the translactonization of erythromycin A enol ether which forms as a result of acid degradation. Copyright © 2001 John Wiley & Sons, Ltd.

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