1,1'-Carbonyldiimidazole → HCID 59201736, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-(trimethylsilyloxy)propyl(methyl)carbamate (79.8 mg, 0.223 mmol) in anhydrous CH2Cl2 (2 mL) were added DIEA (190 μL, 1.12 mmol) and CDI (36.2 mg, 0.223 mmol). The mixture was stirred at 0° C. for 45 min, and methyl (S)-4-(2-chloro-3-fluorophenyl)-4-hydroxy-4-((R)-piperidin-3-yl)butylcarbamate (80.0 mg, 0.223 mmol) was added in one portion and the mixture was allowed to warm to rt and stirred overnight. The reaction was quenched with water and extracted with CH2Cl2 (3×20 mL). The organic extracts were washed with brine and concentrated to give crude product, which was purified by preparative HPLC to afford methyl (S)-4-(2-chloro-3-fluorophenyl)-4-((R)-1-((1S,2R)-1-cyclohexyl-1-hydroxy-3-(N-methyl-N-(t-butoxycarbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)-4-hydroxybutylcarbamate (70 mg, 46.8%). MS (E/Z): 671 (M+H+).

Provenance & Evidence