Isolation and Identification of a Novel Impurity of Erythromycin A 9-Oxime Desosaminehydrazinium Salt

In the manufacturing process for Biaxin ® (clarithromycin), erythromycin-A oxime, an intermediate, is obtained in high yield, when erythromycin-A is treated with hydroxylamine/isopropyl alcohol in the presence of acetic acid. An unusual impurity, the desosamine hydrazinium salt, is generated in this...

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Veröffentlicht in:	Journal of antibiotics 2005-08, Vol.58 (8), p.539-544
Hauptverfasser:	Zhou, Casey Chun, Huang, Xiaomei, Ford, Kelley L, Hollis, L Steven
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetic acid Bacteriology Biomedical and Life Sciences Bioorganic Chemistry communication-to-the-editor Erythromycin - analogs & derivatives Erythromycin - chemical synthesis Erythromycin - chemistry Erythromycin - isolation & purification Hydrazines - chemical synthesis Hydrazines - isolation & purification Life Sciences Magnetic Resonance Spectroscopy Manufacturing industry Medicinal Chemistry Microbiology Organic Chemistry
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Beschreibung
Zusammenfassung:	In the manufacturing process for Biaxin ® (clarithromycin), erythromycin-A oxime, an intermediate, is obtained in high yield, when erythromycin-A is treated with hydroxylamine/isopropyl alcohol in the presence of acetic acid. An unusual impurity, the desosamine hydrazinium salt, is generated in this step of the synthetic pathway, and has been isolated and characterized by using one and two-dimensional NMR spectroscopy in conjunction with MS and EDS.
ISSN:	0021-8820 1881-1469
DOI:	10.1038/ja.2005.75