반응 #9925

반응 방정식

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

sodium carbonate

N-ethoxycarbonyl phthalimide

→

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

수율 68.0%

용매

acetonitrile

water

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 18 hours
2. 2
   기타Most 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
   기타to give a suspension
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 1 hour
7. 7
   여과The suspension was filtered
8. 8
   세척the solid was washed with water (2×10 mL)
9. 9
   기타was dried in a vacuum oven overnight (60° C., <1 torr)

실험 절차

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.

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