Boron tribromide → HCID 58198506, compound

Participants

Reaction Steps

To a solution of 203 mg (0.53 mmol) of N-(5-tert-butyl-isoxazol-3-yl)-2-(4-methoxy-benzenesulfonyl)-2-methyl-propionamide (Example 43, Table 19, prepared according to method A) in DCM (5 mL) were added 0.3 mL (3.18 mmol) of BBr3 at 0° C. under nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was poured onto a saturated aqueous NaHCO3 solution-ice mixture (20 mL). The aqueous mixture was acidified to pH 5 and extracted with DCM (3×15 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was further purified by column chromatography (silica, eluent DCM, 0-20% ethyl acetate) to afford 64 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-(4-hydroxy-benzenesulfonyl)-2-methyl-propionamide.

Provenance & Evidence