Trifluoromethanesulfonic anhydride → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)ethyl pivalate (8J) (200 mg, 0.43 mmol) in dichloromethane (10 mL) and pyridine (0.35 mL) was added Tf2O (0.1 mL, 0.87 mmol) at −78° C. The temperature was slowly raised to 0° C. The mixture was stirred at 0° C. for 2 hours, quenched with slowly addition of NaHCO3 solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to provide a brown colored solid. The obtained residue was purified by flash chromatography to provide the desired product (200 mg, 77%). LCMS-ESI+ (m/z): 602.0, 604.0 (M+H)+.

Provenance & Evidence