Water → (5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Sodium azide (0.596 g, 9.08 mmol) and 18-crown-6 (0.025 g, 0.095 mmol) were added to a solution of {(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate (WO 01/81350 A1) (3.161 g, 8.56 mmol) in DMF (8.5 ml). The reaction mixture was heated to 90° C. under an atmosphere of nitrogen for 19 hours. It was poured into a mixture of ethyl acetate and water and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was removed under vacuum to afford the title compound (1.94 g) as a solid.

Provenance & Evidence