Water → HCID 22262011, compound

Participants

Reaction Steps

To a solution of (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoic acid (4.50 g, 11.1 mmol) in tetrahydrofuran (90 ml) were added diphenylphosphoryl azide (2.62 ml, 12.2 mmol.) and triethylamine (2.32 ml, 16.6 mmol), and the mixture was heated under reflux for 4 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, aqueous sodium hydrogen carbonate solution and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and neutral alumina column chromatography (ethyl acetate). Recrystallization from ethyl acetate-hexane gave the objective substance (4.70 g, 100%).

Provenance & Evidence