Sodium hydride → N-(5R)-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]N-isoxazol-3-yl-carbamic acid tert-butyl ester

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Reaction Steps

To sodium hydride (60% in oil, 9.04 mM) suspended in dry N,N-dimethylformamide (10 ml) under nitrogen, N-isoxazol-3-yl-carbamic acid tert-butyl ester (1.66 g, 9.04 mM) in N,N-dimethylformamide (10 ml) was added dropwise at ambient temperature. Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester (2.5 g, 6.02 mM) in N,N-dimethylformamide (10 ml) was added slowly, and the mixture heated to 75° for 2 hours. After cooling, the mixture was diluted with aqueous sodium bicarbonate (5%, 300 ml), and extracted with ethyl acetate (3×100 ml). The organic phase was washed with water (100 ml) and brine (100 ml), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 50 g silica Mega Bond Elut® column, eluting with dichloromethane. Relevant fractions were combined to give the title compound (1.73 g).

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