Methanol → N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

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Reaction Steps

Lithium butoxide solution (2.5 mL of a 1.0 M THF solution, 2.5 mmol) was added to a cooled (0° C.) solution of [4-(3-aza-bicyclo[3.1.0]hex-3-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester (0.267 g, 0.82 mmol) in DMF (0.6 mL) and MeOH (0.060 mL, 1.64 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.316 g, 1.64 mmol) was then added and the solution allowed to warm to room temperature and stirred for 20 h. Saturated aqueous ammonium chloride (1.0 mL) was added, along with 9 mL of H2O and 8 mL of brine. The solution was extracted with three portions of dichloromethane and the combined organic phases dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (0-3% MeOH-DCM) to provide N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide.

Provenance & Evidence