Hydrochloric Acid → (2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acid

Participants

Reaction Steps

To a solution of ethyl(2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionate (27.5 g, 74.3 mmol) in methanol (300 ml) was added 1N aqueous sodium hydroxide solution (150 ml, 150 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was poured into 1N aqueous hydrochloric acid solution (180 ml), and the mixture was extracted with ethyl acetate (300 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave (2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acid (22.45 g, 88%).

Provenance & Evidence