4-Methylmorpholine → HCID 68157450, compound

Participants

Reaction Steps

A mixture of 4-chloro-N2-phenylbenzene-1,2-diamine (975 mg, 4.46 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (928 mg, 4.90 mmol), HOAt (668 mg, 4.90 mmol), 4-methylmorpholine (1.08 mL, 9.81 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (940 mg, 4.90 mmol) in DCM (30 mL) was stirred at RT for 19 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried and concentrated in vacuo to afford [(S)-1-(4-chloro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester as a purple solid (quantitative). A solution of the compound thus obtained (4.46 mmol) in AcOH (30 mL) was heated at 70° C. for 22 h. After cooling to RT, the volatiles were removed in vacuo and the resulting residue partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The organic layer was washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in DCM) to afford the title compound as a yellow solid (1.20 g, 72% over two steps). LCMS (Method C): RT 3.82 min [M+H]+ 372.3

Provenance & Evidence