Methyl 2,2,2-trichloroacetimidate → Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylate

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Reaction Steps

To a stirred solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (4.7 g, 14.5 mmol) in acetic acid (50 mL) is added methyl trichloroacetimidate (3.1 g, 17.4 mmol). After 3 h at room temperature, the solvent is evaporated, the residue is dissolved in EtOAc, and is washed with Na2CO3 and brine. The organic layer is dried (Na2SO4) and evaporated. The residue is triturated with hexanes to afford the title compound (5.2 g, 80%) as a fine powder. LCMS (Method T), 1.85 min, 450.63 (MH+).

Provenance & Evidence