Triphenylphosphine → (5S)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-one

Participants

Reaction Steps

(5S)-5-(Azidomethyl)-3-[4-(1,1-dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-1,3-oxazolidin-2-one (WO 01/81350 A1) (7 g, 18.2 mmol) was dissolved in water (15 ml) and acetonitrile (150 ml). Triphenylphosphine (5.73 g, 21.9 mmol) was added and the resulting mixture was stirred at room temperature for 2 hours. The solvent was evaporated and the residue purified by flash column chromatography on silica gel with 5% methanol in dichloromethane. The fractions containing product were evaporated to near dryness and treated with ethereal HCl to precipitate the hydrochloride salt of the title compound as a white solid (5.03 g, 70%).

Provenance & Evidence