tert-Butanol → 2-benzyloxy-4-chloro-N-tert-butoxycarbonylaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyloxy-4-chlorobenzoic acid (12.9 g, 46.6 mmol), t-butanol (17.5 mL, 186 mmol) and triethylamine (7.79 mL, 55.9 mmol) in toluene (250 mL) is added DPPA (11.1 mL, 51.3 mmol) and the mixture is stirred at 85° C. for 3 h then at 65° C. for 48 h. The mixture is diluted with EtOAc (500 mL) and is washed with 1N HCl (3×150 mL), NaHCO3 (3×150 mL) and brine (150 mL). The organic phase is dried over sodium sulfate and the solvent evaporated to give a brown solid which is triturated with hexane to give the title compound: (M−1)−=332.

Provenance & Evidence