1,1'-Carbonyldiimidazole → tert-butyl (S)-2-(3-(3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate

Participants

Reaction Steps

At 0° C., CDI (48.6 mg, 0.3 mmol) was added to a solution of (S)-tert-butyl 2-amino-3-cyclohexylpropyl(methyl)carbamate (81 mg, 0.3 mmol), prepared using procedures described in U.S. Prov. App No. 05/036,230 (PCT App No. 60/616,770), and DIEA (161 mg, 1.25 mmol) in anhydrous CH2Cl2 (8 mL) followed by stirring for 1 h. The solution was added to methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate (75 mg, 0.25 mmol) in anhydrous CH2Cl2 (4 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. After the reaction was completed, the solvent was removed in vacuo. The product was purified with preparative TLC to afford tert-butyl (S)-2-(3-(3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate (70 mg, 50%).

Provenance & Evidence