1-Heptanamine → 4-{[(Heptylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

Participants

Reaction Steps

A yellow solution of VII (87 mg, 0.255 mmol), n-heptylamine (31 mg, 1.05×0.255 mmol) and triethylamine (26 mg, 36 μL, 0.255 mmol) in 3 mL of dichloromethane was stirred at room temperature overnight. The reaction was worked up as described for 7. The product was purified by preparative thick layer chromatography using dichloromethane/diisopropyl ether, 9:1, v/v, as the developing solvent. The result was 58 mg (67%) of 6 as a clear oil: Rf=0.53 (dichloromethane/acetone, 97:3, v/v); 1HNMR (CDCl3) δ 6.98 (d, 3J=8.0 Hz, 1H), 6.94 (s, 1H), 6.91 (d, 3J=8.0 Hz, 1H), 4.98 (s, 2H), 4.73 (bs 1H, NH), 3.81 (s, 3H), 3.18-3.14 (m, 2H), 2.29 (s, 3H), 1.50-1.43 (m, 2H), 1.31-1.19 (m, 8H) and 0.85 (t, 3J=7.0 Hz, 3H). Exact mass (FAB+) calculated for C18H27NO5 [M+] 337.1889. found 337.1895.

Provenance & Evidence