Benzoic acid, 3-amino-, methyl ester → 3-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of the (4-adamantan-1-yl-phenoxy)-acetic acid (140 mg, 0.5 mmol) and 3-aminobenzoic acid methyl ester (110 mg, 0.75 mmol) in DMF (5.0 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (144.0 mg, 0.75 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (101 mg, 0.75 mmol), and N,N-diisopropylethylamine (DIPEA) (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=15:3:1) gave 3-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (160 mg, 76% yield).

Provenance & Evidence