[(S)-1-(2-Chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester → [(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

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Reaction Steps

A solution of [(S)-1-(2-chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester (1.58 g, 4.05 mmol) in AcOH (25 mL) was stirred for 18 h at 65° C. After cooling to RT, volatiles were evaporated under reduced pressure and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM) affording [(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester as an off-white solid (1.41 g, 93%). LCMS: RT 3.90 min [M+H]+ 372.2.

Provenance & Evidence