Methanol → HCID 135870805, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 200 mg of 3-{4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-4H-[1,2,4]oxadiazol-5-one in 6 ml of dichloromethane cooled to −70° C. was added 0.8 mL of a 1 M solution of boron tribromide in dichloromethane. After stirring for 45 minutes at −60° C., the solution was poured into a mixture of methanol and a saturated aqueous solution of sodium hydrogenocarbonate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10) then crystallized from dichloromethane/diisopropylether to give 18 mg of 3-{2-chloro-4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Provenance & Evidence