A long-range 15N-NMR study of the oxazolidinone antibiotic zyvox® and the major thermal degradation products

✍ Scribed by C. E. Hadden; P. B. Bowman; W. H. Duholke; J. E. Guido; B. D. Kaluzny; R. H. Robins; D. J. Russell; S. M. Sims; T. J. Thamann; G. E. Martin

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 350 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370636

✦ Synopsis

Abstract

The structures of the major thermal degradation products of linezolid (Zyvox^®^, PNU‐100766) are reported. Following hydrolytic decarboxylation, the remaining oxazolidinone‐derived skeleton of the antibiotic underwent a variety of acetyl migrations prior to deacetylation. Three of the degradation products are structural isomers. Structural characterization of the degradants was accomplished via the concerted analysis of 2D NMR, mass spectrometric, and infrared data. Direct and long‐range ^1^H‐^15^N heteronuclear shift correlation experiments at natural abundance were performed on linezolid as well as each of the isolated products of the degradation cascade. ^15^N chemical shifts for linezolid and each of the degradants, as well as the observed long‐range ^1^H‐^15^N coupling pathways are reported.