Ammonia → HCID 178440691, compound

Participants

Reaction Steps

To a solution of benzyl (3S)-3-amino-3-(5-tert-butyl-1H-benzimidazol-2-yl)-2,2-dimethylpropanoate (Preparation 13, 150 mg, 0.312 mmol) in THF (10 mL) was added freshly condensed liquid NH3 (20 mL) at −78° C. and the reaction was stirred at room temperature for 24 hours. The reaction mixture was evaporated and purified by preparative TLC eluting with 70% EtOAc in petroleum ether. The residue was dissolved in dioxane (6 mL), cooled to 0° C. and treated with 2N HCl in dioxane (4 mL). The reaction was stirred at room temperature for 4 hours before concentrating in vacuo. The residue was purified through an SCX cartridge to afford the title compound (25 mg, 30%).

Provenance & Evidence