4-Methylmorpholine → HCID 68157988, compound

Participants

Reaction Steps

A mixture of 4-fluoro-N2-phenylbenzene-1,2-diamine (450 mg, 2.2 mmol), (S)-2-(tertbutoxycarbonylmethylamino)propionic acid (0.50 g, 2.4 mmol), HOAt (0.33 g, 2.4 mmol), 4-methylmorpholine (0.5 mL, 4.8 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.46 g, 2.4 mmol) in DCM (10 mL) was stirred at RT for 2 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer 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)-1-(4-fluoro-2-phenylaminophenylcarbamoyl)ethyl]methylcarbamic acid tert-butyl ester (0.781 g, 92%). LCMS (Method J): RT 3.92 min [M+H]+ 388.1.

Provenance & Evidence