Hydrochloric Acid → Methyl (2S,3R)-1-((1R,4S)-3-(5-(4-bromo-2-fluorophenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-3-methoxy-1-oxobutan-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(1R,4S)-tert-butyl 3-(5-(4-bromo-2-fluorophenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate was dissolved in DCM (5 mL) and treated with HCl (4M in dioxane, 1 mL). After 1 h, the reaction mixture was concentrated. The residue was treated (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (76 mg, 0.406 mmol), HATU (154 mg, 0.406 mmol) and DMF (4 mL). The stirred reaction mixture was cooled to 0° C., DIPEA (0.35 mL, 2.03 mmol) was added dropwise and the reaction mixture was warmed to RT. After 20 min, it was diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (0% to 33% MeOH/EtOAc) to afford the title compound (162 mg, 78%).

Provenance & Evidence