Triethylamine → (4RS,5SR)-5-(3-chlorophenyl)-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidin-2-one

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Reaction Steps

To a solution of (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid (2.75 g, 6.50 mmol) in tetrahydrofuran (70 ml) were added triethylamine (1.36 ml, 9.75 mmol) and diphenylphosphoryl azide (1.54 ml, 7.15 mmol), and the mixture was heated under reflux for 4 hrs. The solvent was evaporated and the residue was diluted with ethyl acetate, washed with water, saturated. aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue as recrystallized from hexane-ethyl acetate to give (4RS,5SR)-5-(3-chlorophenyl)-4-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]-1,3-oxazolidin-2-one (2.54 g, 93%) as colorless crystals.

Provenance & Evidence