2-chloro-N-(1,2-oxazol-3-yl)acetamide → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-(isoxazol-3-ylamino)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane chloride

Participants

Reaction Steps

2-Chloro-N-(isoxazol-3-yl)acetamide (18.3 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-(isoxazol-3-ylamino)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane chloride (26.2 mg, 38.4% yield).

Provenance & Evidence