Water → (4RS,5RS)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

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Reaction Steps

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (4.30 g, 12.6 mmol) in tetrahydrofuran (80 ml) were added diphenylphosphoryl azide (3.0 ml, 13.8 mmol) and triethylamine (2.63 ml, 18.8 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was diluted with water (300 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (3.55 g, 83%).

Provenance & Evidence