4-Methylmorpholine → HCID 68157577, compound

Participants

Reaction Steps

A mixture of 4-methyl-N2-phenylbenzene-1,2-diamine (600 mg, 3.03 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (861 mg, 4.55 mmol), HOAt (453 mg, 3.33 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (874 mg, 4.55 mmol) and 4-methylmorpholine (0.74 mL, 6.67 mmol) in anhydrous DCM (20 mL) was stirred at RT for 1.5 h. Volatiles were removed under reduced pressure and the resulting residue was dissolved in AcOH (10 mL) and heated to 70° C. for 20 h. After cooling to RT, volatiles were removed in vacuo and the residue was dissolved in EtOAc (100 mL) and washed with a saturated solution of NaHCO3 (2×100 mL). The organic layer was then washed with brine, dried (Na2SO4) and then concentrated in vacuo. The resulting residue was absorbed onto HM-N and the solvent was removed in vacuo. The product was purified by column chromatography (Si—PCC, gradient 10-60% EtOAc in cyclohexane) affording [(S)-1-(6-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (969 mg, 92%). LCMS: RT 3.10 min [M+H-tBu]+ 352.1.

Provenance & Evidence