A long-range N-15-NMR study of the oxazolidinone antibiotic Zyvox (R) and the major thermal degradation products

The structures of the major thermal degradation products of linezolid (Zyvo x(R), PNU-100766) are reported. Following hydrolytic decarboxylation, the r emaining oxazolidinone-derived skeleton of the antibiotic underwent a varie ty of acetyl migrations prior to deacetylation. Three of the degradation pr oducts are structural isomers. Structural characterization of the degradant s was accomplished via the concerted analysis of 2D NMR, mass spectrometric , and infrared data. Direct and long-range H-1-N-15 heteronuclear shift cor relation experiments at natural abundance were performed on linezolid as we ll as each of the isolated products of the degradation cascade. N-15 chemic al shifts for linezolid and each of the degradants, as well as the observed long-range H-1-N-15 coupling pathways are reported.