2-Ethylhexylamine → 4-{[(2-Ethylhexylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

Participants

Reaction Steps

To a stirred yellow solution of VII (298.2 mg, 0.873 mmol) in anhydrous THF (10 mL) was added 2-ethylhexylamine (124 mg, 157 μL 1.1×0.873 mmol) and then, dropwise, triethylamine (97 mg, 135 μL, 1.1×0.873 mmol). The solution was stirred for 3 hours at room temperature. The colorless solution was then diluted with diethyl ether and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (6:4, v/v) to give 9 as 207.2 mg (68%) of a clear, light yellow oil: Rf=0.60 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8.0 Hz, 1H), 6.95 (d, 4J=1.75 Hz, 1H), 6.92 (dd, 3J=8.0 Hz, 4J=1.72 Hz, 1H), 5.04 (s, 2H), 4.67 (bs, 1H, NH), 3.82 (s, 3H), 3.16-3.08 (m, 2H), 2.29 (s, 3H), 1.43-1.35 (m, 1H), 1.33-1.119 (m, 8H) and 0.867 (apparent triplet, 3J=7.2 Hz, 6H). Exact mass (FAB+) calculated for C19H30NO5 [M+H] 352.2118. found 352.2101.

Provenance & Evidence