Hydrochloric Acid → (S)-2-(4-Fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-N-hydroxy-butyramide

Participants

Reaction Steps

To a solution of (R)-4-benzyl-3-((S)-2-(4-fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-butyryl)-oxazolidin-2-one (0.033 g, 0.0601 mmol) in 2.5 mL of THF/MeOH/50% NH2OH—H2O (2:2:1), was added KCN (0.001 g, 0.006 mmol). After stirring at room temperature overnight, the reaction mixture was acidified with concentrated HCl to pH=2 and filtered. The product was isolated by RP-HPLC eluting with 20-100% acetonitrile (0.025% TFA)/water (0.025% TFA) to give the title compound as an off-white solid (0.016 g, 66% yield). LC-MS: tR=5.5 min, m/z 405 (M+H)+.

Provenance & Evidence