تفاعل #520502
ord-7a5505813a5c42ec9a6eeb802c2c4062
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
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المعالجة
- 1درجة الحرارةto cool to room temperature
- 2استخلاصThe resulting mixture was extracted with EtOAC (3×30 mL)
- 3غسيلThe combined ethyl acetate extracts were washed with water (30 mL), brine (30 mL)
- 4تجفيفdried over magnesium sulfate
- 5أخرىThe solvent was removed in vacuo
- 6أخرىthe residue was purified by chromatography (Silica gel, methylene chloride: EtOAC 8:2)
- 7أخرىto give N-{2-1-(3-cyclopentyloxy-4-meth-oxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide (1.3 g, 73%) as a white solid
الإجراء التجريبي
A stirred mixture of 4-amino-4-(3-cyclopentyloxy-4-methoxyphenyl)butan-2-ol hydrochloride(1.20 g, 3.80 mmol), 3-acetamidophthalic anhydride (0.78 g, 3.80 mmol) and triethylamine (0.38 g, 3.80 mmol) in DMF (15 mL) was heated at 80-90° C. for 7 hours. The mixture was allowed to cool to room temperature and poured into water (80 mL). The resulting mixture was extracted with EtOAC (3×30 mL). The combined ethyl acetate extracts were washed with water (30 mL), brine (30 mL) and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by chromatography (Silica gel, methylene chloride: EtOAC 8:2) to give N-{2-1-(3-cyclopentyloxy-4-meth-oxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide (1.3 g, 73%) as a white solid: 1H NMR (CDCl3) δ9.53 (s, 1H), 8.71 (d, J=8.4 Hz, 1H), 7.63 (t, J=7.7 Hz, 1H), 7.48 (d, J=7.3 Hz, 1H), 7.08-7.03 (m, 2H), 6.82 (d, J=8.2 Hz, 1H), 5.57-5.51 (dd, J=4.2, 11.6 Hz, 1H), 4.78 (m, 1H), 3.81 (s, 3H), 3.77-3.74 (m, 1H), 2.91-2.81 (m, 1H), 2.25 (s, 3H), 2.13-1.60 (m, 10H), 1.29 (d, J=6.1 Hz, 3H); 13C NMR (CDCl3) δ170.38, 169.21, 168.06, 149.70, 147.50, 137.33, 135.84, 131.54, 131.20, 124.71, 120.28, 117.93, 115.31, 115.07, 111.55, 80.45, 64.89, 55.97, 51.35, 39.92, 32.73, 24.91, 24.04, 23.76, 21.02.