反应详情

To a mixture of [4-(1-adamantyl)phenoxy]acetic acid (143.2 mg, 0.5 mmol), 4-aminobenzoic acid methyl ester (113.4 mg, 0.5 mmol), N-3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (143.8 mg, 0.75 mmol) and 1-hydroxybenzothiazole (HOBt) (101.4 mg, 0.75 mmol) in DMF (6 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (97.0 mg, 0.13 mL, 0.75 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:MeOH=6:3:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (108.3 mg, 51.7% yield).

1. distillationredistilled (DIPEA) (97.0 mg, 0.13 mL, 0.75 mmol)
2. custompartitioned between ethyl acetate and 10% HCl
3. washThe organic phase was washed with brine
4. dry with materialdried (MgSO4 anh)
5. concentrationconcentrated
6. customThe residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)