Isatoic Anhydride → tert-Butyl N-(2-aminobenzoyl)glycinate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of isatoic anhydride (25 g, 0.15 mol) in DMF (250 ml), glycine tert butyl ester (30.64 g, 0.18 mol) is added, followed by the dropwise addition of triethylamine (52 ml, 0.37 mol) over a period of 30 minutes. The resulting suspension is heated at 50° C. for 3 hours, 60° C. for 30 minutes, then at 70° C. for 30 minutes. The reaction mixture is then allowed to cool to RT and treated with water (300 ml). The resulting solution is stirred at RT for 30 minutes, diluted further with water (200 ml), and the product extracted with EtOAc (2×500 ml). The organic extracts are combined, washed with water (2×300 ml), brine (1×300 ml), dried (MgSO4), filtered, concentrated in vacuo, and dried under vacuum to give the title compound as a peachy white solid.

Provenance & Evidence