Triacetoxyperiodinane → 2-chloro-N-(4-(((2-oxo-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

Participants

Reaction Steps

a mixture of 2-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino) carbonyl)phenyl)benzamide (294 mg, 719 μmol) and Dess-Martin periodinane (335 mg, 791 μmol) in 5 mL dichloromethane+1 mL DMF was stirred at room temperature for 2 hours then diluted with 20 mL ethyl acetate and washed with 10 mL each water and brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow solid. The solid was slurried in hot ethyl acetate and left to equilibrate to room temperature. After 48 h, the solid was collected by filtration, rinsing with ethyl acetate and drying over a stream of air (200 mg, 68%). ESI+ m/z=407.0 [MH]+.

Provenance & Evidence