Hydrochloric Acid → 2-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid

Participants

Reaction Steps

A solution of 2-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester (30.5 mg, 0.07 mmol) in 1,4-dioxane/H2O (3:1, 3 mL) added LiOHH2O (8.4 mg, 0.2 mmol) at room temperature. The resulting mixture was stirred overnight, and then acidified with 10% HCl to PH 2. Ethyl acetate was added and the organic layer was separated. The organic layer was washed with water, and dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:EtOAc:MeOH=6:3:1) to gave 2-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid as a white solid (18.5 mg, 62.5% yield).

Provenance & Evidence