تفاعل #9925

معادلة التفاعل

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

sodium carbonate

N-ethoxycarbonyl phthalimide

→

3-(3-cyclopentyloxy-4-methoxy-phenyl)-3-phthalimidopropanoic acid

المردود 68.0%

المذيبات

acetonitrile

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 18 hours
2. 2
   أخرىMost of solvent was removed in vacuo
3. 3
   workup.ADDITIONTo the solution was added hydrochloric acid (6N) until the pH of solution <1
4. 4
   أخرىto give a suspension
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 1 hour
7. 7
   ترشيحThe suspension was filtered
8. 8
   غسيلthe solid was washed with water (2×10 mL)
9. 9
   أخرىwas dried in a vacuum oven overnight (60° C., <1 torr)

الإجراء التجريبي

A mixture of 3-amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (3.00 g, 10.8 mmol) and sodium carbonate (1.20 g, 11.3 mmol) in acetonitrile (30 mL) and water (30 mL) under nitrogen was stirred at room temperature for 15 minutes. To the resulting solution was added N-ethoxycarbonyl phthalimide (2.36 g, 10.8 mmol). The resulting mixture was stirred at room temperature for 18 hours. Most of solvent was removed in vacuo. To the solution was added hydrochloric acid (6N) until the pH of solution <1 to give a suspension and stirring was continued for 1 hour. The suspension was filtered, the solid was washed with water (2×10 mL), and then was dried in a vacuum oven overnight (60° C., <1 torr) to afford 3-(3-cyclopentyloxy-4-methoxy-phenyl)-3-phthalimidopropanoic acid as a white solid (3.0 g, 68% yield): mp, 168.0–169.0° C.; 1H NMR (DMSO-d6) δ 1.55–1.88 (m, 8H, C5H8), 3.27 (dd, J=6.9, 16.5 Hz, 1H, CHH), 3.51 (dd, J=8.9, 16.5 Hz, 1H, CHH), 3.71 (s, 3H, CH3), 4.71–4.75 (m, 1H, CH), 5.61 (dd, J=6.9, 8.8 Hz, 1H, NCH), 6.87–6.95 (m, 2H, Ar), 7.03 (br s, 1H, Ar), 7.81–7.91 (m, 4H, Ar), 12.4 (br s, 1H, OH); 13C NMR (DMSO-d6) δ 23.51, 32.14, 32.17, 36.07, 50.08, 55.52, 79.57, 112.15, 113.97, 119.39, 123.17, 131.09, 131.19, 134.66, 146.77, 149.16, 167.67, 171.72; Anal Calcd for C23H23NO6: C, 67.47; H, 5.66; N, 3.42. Found: C, 67.21; H, 5.46; N, 3.45.

المصدر