4-Methylmorpholine → HCID 68157104, compound

Participants

Reaction Steps

A mixture of 4-methyl-N1-phenylbenzene-1,2-diamine (500 mg, 2.52 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (524 mg, 2.77 mmol), HOAt (377 mg, 2.77 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (532 mg, 2.77 mmol) and 4-methylmorpholine (0.609 mL, 5.54 mmol) in anhydrous DCM (20 mL) was stirred at RT for 20 h. The reaction mixture was diluted with DCM (100 mL) and washed with a saturated solution of NaHCO3. The organic layer was then dried and concentrated in vacuo. 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 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 purified by column chromatography (Si—PCC, gradient 10-60% EtOAc in cyclohexane) affording [(S)-1-(5-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (912 mg, quantitative). LCMS: RT 3.02 min [M+H-tBu]+ 352.1.

Provenance & Evidence