HOAt → [(S)-2-ethoxy-1-(4-fluoro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-N2-phenylbenzene-1,2-diamine (562 mg, 2.8 mmol) in DCM (18 mL) at 0° C. were added (S)-2-tertbutoxycarbonylamino-3-ethoxypropionic acid (720 mg, 3.1 mmol), HOAt (0.420 g, 3.1 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.59 g, 3.1 mmol) and the resulting mixture stirred at 0° C. for 1 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic fraction was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) to afford [(S)-2-ethoxy-1-(4-fluoro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (770 mg, 66%). LCMS (Method B): RT 3.87 min [M+H]+ 418.3

Provenance & Evidence