Hydrochloric Acid → 4-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]benzoic acid

Participants

Reaction Steps

3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (151.8 mg, 0.35 mmol) in 1,4-dioxane/H2O (10 ml) was treated with KOH (290.7 mg, 5.18 mmol) at 60° C. for 3 h. The reaction mixture was then acidified with 10% HCl to PH 2, and then partitioned between ethyl acetate and brine. The organic phase was washed with water, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CH2:MeOH 4:1) to give 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid as a white solid (110.4 mg, 75.10% yield).

Provenance & Evidence