Methanol → HCID 68786209, compound

Participants

Reaction Steps

Boron tribromide (1 M in dichloromethane, 5.4 mL, 5.44 mmol) was added dropwise over 5 min to a suspension of 2-[2-(2-ethoxy-phenyl)-ethenesulfonylamino]-benzenesulfonamide (example 222) (0.21 g, 0.54 mmol) in dichloromethane (10 mL) at −78° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. Cooled to −20° C. and methanol (5 mL) was added slowly. The resulting solution was warmed up to room temperature and heated at 50° C. for 1 hour. The volatiles were removed under reduced pressure and the residue was taken up in methanol (5 mL). The mixture was concentrated in vacuo and the process was repeated once more. The residue was taken up in water (5 mL) and ethyl acetate (15 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave 31 mg (16% yield) of the title compound.

Provenance & Evidence