Lithium Hydroxide → 4-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution 2M of lithium hydroxide (283 μL, 566 μmoles) is added to a solution of 4-{4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid ethyl ester (isomer A, 60 mg, 113 μmoles) in 1,4-dioxane (2 mL) and the mixture is stirred at 90° C. overnight. The organic solvent is removed and HCl (1M) is added until the solution reaches pH 3-4. The solid is filtered and purified via flash chromatography (12 g silica) eluting with a gradient of dichloromethane:ethyl acetate from 10% to 20% to provide the title compound (50 mg, 88%) as a white solid. ES/MS m/z 501.0 (M+1).

Provenance & Evidence