反応 #9923

反応方程式

3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid

4-methylphthalic anhydride

ethyl acetate

hexane

→

3-(3-ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid

収率 71.0%

溶媒

acetic acid

water

反応条件

後処理

1. 1
   温度to reflux under nitrogen for 18 hours
2. 2
   その他The solvent was removed in vacuo
3. 3
   その他to give an oil
4. 4
   ろ過The resulting suspension was filtered
5. 5
   洗浄The solid was washed with water (3×10 mL) and hexane (3×10 mL)
6. 6
   その他was dried in a vacuum oven overnight (60 ° C., <1 torr)

実験手順

A stirred solution of 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (3.00 g, 12.5 mmol) and 4-methylphthalic anhydride (2.13 g, 12.5 mmol, 95%) in acetic acid was heated to reflux under nitrogen for 18 hours. The mixture was allowed to cool to room temperature. The solvent was removed in vacuo to give an oil. The resulting oil was stirred with ethyl acetate (10 mL), hexane (10 mL) and water (30 mL) for 30 minutes. The resulting suspension was filtered. The solid was washed with water (3×10 mL) and hexane (3×10 mL), and then was dried in a vacuum oven overnight (60 ° C., <1 torr) to give 3-(3-ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid as a white solid (3.4 g, 71% yield): mp, 134.0–136.0° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 2.47 (s, 3H, CH3), 3.23 (dd, J=6.7, 16.5 Hz, 1H, CHH), 3.50 (dd, J=9.2, 16.5 Hz, 1H, CHH), 3.72 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.58 (dd, J=6.7, 9.1 Hz, 1H, NCH), 6.90–6.95 (m, 2H, Ar), 7.01 (br s, 1H, Ar), 7.61–7.76 (m, 3H, Ar), 12.4 (br s, 1H, OH); 13C NMR (DMSO-d6) δ 14.65, 21.32, 36.09, 50.04, 55.45, 63.72, 111.79, 112.15, 119.29, 123.08, 123.58, 128.51, 131.35, 131.49, 134.95, 145.63, 147.75, 148.53, 167.67, 167.78, 171.72; Anal Calcd for C21H21NO6: C, 65.79; H, 5.52; N, 3.65. Found: C, 65.46; H, 5.57; N, 3.31.

出典