Water → HCID 22262075, compound

Participants

Reaction Steps

To a solution of 3-(6-chloro-2-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (3.1 g, 8.6 mmol) in tetrahydrofuran (100 ml) were added diphenylphosphoryl azide (2.0 ml, 9.5 mmol) and triethylamine (1.8 ml, 12.9 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool, water (150 ml) was added, and the mixture was extracted with ethyl acetate (150 ml×2). The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give 5-(6-chloro-2-pyridyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (1.18 g, 38%, (4RS,5RS) form: (4RS,5SR) form=3:2).

Provenance & Evidence