Reacción #9925

Ecuación de reacción

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

sodium carbonate

N-ethoxycarbonyl phthalimide

→

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

Rendimiento 68.0%

Disolventes

acetonitrile

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente