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La aminación reductiva sobre eritromicina como ruta alternativa para la obtención de eritromicilamina, intermediario en la síntesis de diritromicina

This paper is available in a repository.
This paper is available in a repository.

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Abstract

The erythromycin is a macrolide antibiotic of ample spectrum, produced by a stock of Streptomyces erythreus. It has reached great importance thanks to its activity against prevalent pathogens like Legionella, Helicobacter, Mycoplasma, and Chlamydia. In the last twenty years, the erythromycin has been committed with substantial efforts to improve its structural and biological properties. Dirithromycin is the 9N-11-O-oxazine derivative, obtained out of condensation of 9(S)-erythromycyclamine with the 2-(2- methoxyethoxy) acetaldehyde. It is a macrolide antibiotic of new generation; its spectrum of action is similar to that of erythromycin, although dirithromycin presents higher and more prolonged concentrations in the weaves. Erythromycyclamine is the synthetic intermediary key in the synthesis of dirithromycin and, commonly, derived from the eritromicina via oxime or his hydrazones implying several passages of synthesis. In this work, it was considered to shorten the synthesis mechanism obtaining erythromycyclamine directly via erythromycin, a reaction of reductive amination forming the corresponding amina with ammonia and reducing it with Sodium Cyanoborohydride, according to a method proposed by Borch and collaborators. Two products of acid-base extractions were obtained. When subject to IR spectrometry, they revealed the presence of the group carbonyl wanted to be amined, and the absence of the bands of the amino group. This indicates that the amination was not made and that the erythromycin was degraded by an unknown mechanism to products not characterized yet.