[(S)-1-(2-Benzylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

[(S)-1-(2-Benzylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (1.7 g, 4.39 mmol) was dissolved in acetic acid (15 mL) and heated at 70° C., overnight, under an atmosphere of nitrogen. The reaction mixture was then heated at 80° C. for 6 h. The resultant mixture was allowed to cool to RT and was concentrated in vacuo. The residue was purified by column chromatography (silica gel, gradient 0-50% EtOAc in cyclohexane) to afford the title compound as an off-white solid (0.88 g, 55%). 1H NMR (CDCl3, 400 MHz): δ 7.68 (1H, dd, J=8.81, 4.79 Hz), 7.34-7.26 (3H, m), 7.08-6.95 (3H, m), 6.90 (1H, dd, J=8.69, 2.43 Hz), 5.43 (2H, d, J=5.40 Hz), 5.18-5.06 (1H, m), 1.53 (3H, d, J=6.73 Hz), 1.37 (9H, s).

Provenance & Evidence