Methyl Anthranilate → 2-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester

Participants

Reaction Steps

To a mixture of [4-(1-adamantyl)phenoxy]acetic acid (85.9 mg, 0.30 mmol), 2-amino-benzoic acid methyl ester (0.07 mL, 0.54 mmol), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (103.5 mg, 0.54 mmol) and 1-hydroxybenzotriazole (HOBt) (73.0 mg, 0.54 mmol) in DMF (3.6 mL) was added N,N-diisopropylethylamine, redistill (DIPEA) (69.8 mg, 0.10 mL, 0.54 mmol). The mixture was stirred overnight, and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeEOH=12:3:1) to give 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (46.4 mg, 3.69% yield).

Provenance & Evidence