Deng Zhi
2003
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0
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Journal
Chinese Journal of Medicinal Chemistry
Abstract
Aim To synthesize erythromycin A 9 oxime(1)which is the common intermediate of some novel antibiotics such as clarithromycin,azithromycin,rozithromycin,flurithromycin and dirithromycin by a novel method.Methods The target compound(1)was prepared from erythromycin A(3)and hydroxylamine hydrochloride in a novel acid base buffer.The relationships of the purity of compound 1 and the pH,the reactive temperature and the quantity of hydroxylamine hydrochloric were studied.The mechanism of oximation reaction of erythromycin A was deduced.The main impurity,which is 8,9 dehydro erythromycin A 6,9 hemiketal(2) and involved in the synthesis of erythromycin oxime was separated and purified.Results The yield and purity of 1 were more than 95% and 92% respectively.The mass spectra,infrared spectra and complete proton and carbon NMR of compounds 1 and 2 were consistent with the results reported by literatures completely.Conclusion The acid base buffer can prevent greatly the decomposition of erythromycin A.The yield and purity of 1 were increased by the novel method.