Water → (4RS,5SR)-5-(2-fluoropyridin-4-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one

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Reaction Steps

To a solution of (2RS,3RS)-3-(2-fluoropyridin-4-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid (2.0 g, 5.11 mmol) in tetrahydrofuran (50 ml) were added diphenylphosphoryl azide (1.21 ml, 5.62 mmol) and triethylamine (1.07 ml, 7.67 mmol), and the mixture was heated under reflux for 2 hrs. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1). Recrystallization from ethyl acetate-hexane gave (4RS,5SR)-5-(2-fluoropyridin-4-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one (1.36 g, 69%).

Provenance & Evidence