Reaktion #9956

Reaktionsgleichung

3-(3-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid

carbonyldiimidazole

hydroxylamine hydrochloride

→

3-(3-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide

Ausbeute 70.0%

Lösungsmittel

THF

Reaktionsbedingungen

Vorschrift

3-(3-Acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(3-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (3.0 g, 6.5 mmol), carbonyldiimidazole (1.16 g, 7.12 mmol) and hydroxylamine hydrochloride (0.56 g, 8.07 mmol) in THF (20 mL) to afford 3-(3-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide as a white solid (2.17 g, 70%): mp, 156.5–158.0° C.; 1H NMR (DMSO-d6) δ 1.55–1.87 (m, 8H, C5H8), 2.19 (s, 3H, CH3), 3.11 (d, J=7.8 Hz, 2H, CH2), 3.70 (s, 3H, OCH3), 4.50–4.84 (m, 1H, OCH), 5.64 (t, J=7.8 Hz, 1H, CH), 6.80–6.90 (m, 3H, Ar), 7.56 (d, J=7.3 Hz, 1H, Ar), 7.77 (t, J=7.9 Hz, 1H, Ar), 8.44 (d, J=8.4 Hz, 1H, Ar), 8.81 (s, 1H, NH), 9.72 (s, 1H, OH), 10.95 (s, 1H, CONH); 13C NMR (DMSO-d6) δ 23.5, 24.2, 32.2, 34.1, 50.0, 55.6, 79.6, 112.1, 114.2, 117.9, 119.7, 125.9, 130.9, 131.4, 135.8, 136.4, 146.7,;149.2, 165.9, 167.1, 168.2, 169.2; Anal. Calcd. for C25H27N3O7: C, 61.10; H, 5.76; N, 8.55. Found: C, 61.43; H, 5.62; N, 8.50.

Quelle