Trifluoroborane-methyl sulfide → N-[3,5-dichloro-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)benzoyl]glycine

Participants

Reaction Steps

Boron trifluoride dimethyl sulfide (1.48 mL, 13.7 mmol) was added at 4° C. to a stirred solution of methyl-N-[3,5-dichloro-4-(5-isopropyl-4-methoxy-3-methylphenoxy)benzoyl]glycine (155 mg, 0.352 mmol) and dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 24 hours and then treated with ice-water (30 mL), extracted with ethyl acetate and concentrated. The residue was purified on column (MPLC, silica gel, chloroform/methanol/acetic acid, gradient elution from 1/0/0 to 95/5/0.5) to give 110 mg (76%) of N-[3,5-dichloro-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)benzoyl]glycine. LC-MS (ES−1): m/z 410.

Provenance & Evidence