Réaction #9926

Équation de réaction

3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid

hydroxylamine hydrochloride

→

3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide

Rendement 93.1%

Solvants

tetrahydrofuran

Conditions de réaction

Mode opératoire

3-(3-Cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (1.50 g, 3.67 mmol), N,N′-carbonyldiimidazole (653 mg, 4.03 mmol) and hydroxylamine hydrochloride (308 mg, 4.43 mmol) in tetrahydrofuran (5 mL) to afford 3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide as a white solid (1.45 g, 93% yield): mp, 169.0–171.0° C.; 1H NMR (DMSO-d6) δ 1.54–1.85 (m, 8H, C5H8), 3.09 (d, J=7.9 Hz, 2H, CH2), 3.69 (s, 3H, CH3), 4.70–4.72 (m, 1H, CH), 5.67 (t, J=7.9 Hz, 1H, NCH), 6.87 (br s, 2H, Ar), 7.01 (br s, 1H, Ar), 7.79–7.87 (m, 4H, Ar), 8.78 (br s, 1H, OH), 10.58 (1H, NH); 13C NMR (DMSO-d6) δ 23.51, 32.17, 34.23, 50.19, 55.53, 79.57, 112.08, 114.16, 119.69, 123.11, 131.16, 131.20, 134.59, 146.73, 149.17, 166.01, 167.63; Anal Calcd for C23H24N2O6: C, 65.08; H, 5.70; N, 6.60. -Found: C, 64.73; H, 5.60; N, 6.53.

Source