Oxazolidinones show potent activity against vancomycin-resistant Staphyloco
ccus aureus (VRSA) species, and are currently under active development. We
present NMR spectroscopy and molecular dynamics calculation studies on N-(1
-benzoyl-3-pyrrolidinyl) benzamide, an oxazolidinone derivative with substi
tution at the amine group of 3-pyrrolidinamine. The H-1-NMR and C-13-NMR sp
ectra exhibited two sets of peaks, one major and one minor, giving rise to
the existence of isomers at room temperature. In order to deduce the nature
of its isomeric distribution, a series of derivatives were synthesized and
analyzed using NMR spectroscopy and computer-aided molecular modeling (CAM
M) simulations. The results suggest that rotation of the benzoyl group atta
ched to the secondary amine in N-(1-benzoyl-3-pyrrolidinyl) benzamide is re
sponsible for conformational heterogeneity.