Chemistry and X-ray crystallographic structure of N-protected (5-oxo-1,3-oxazolidin-4-yl)acetic acids: versatile intermediates in the synthesis of peptidomimetics

Abstract

The X-ray crystal structures of [(2′R,4′S)-3′-benzoyl-4′- benzyl-5′-oxo-2′-phenyloxazolidin-4′-yl]acetic acid 16 and [(2′S,4′R)-3′-acetyl-4′- benzyl-5′-oxo-2′-phenyloxazolidin-4′-yl]acetic acid 19 have been determined and their conformations compared to those of related oxazolidinones. Compounds of the type 16 and 19 have also been shown to be useful precursors to succinimide-based peptidomimetics possessing conformational restriction and latent reactivity.