反应详情

温度

0 °C

As mentioned above, 5-hydroxy-L-tryptophan methyl ester hydrochloride (350 mg, 1.29 mmol) and ferulic acid (251 mg, 1.29 mmol) were dissolved in a mixed solvent of dichloromethane (6 ml) and N,N-dimethylformamide (6 ml), and the solution was maintained at 0° C. To this solution were added triethylamine (198 μl, 1.4 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 217 mg, 1.4 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI HCl, 217 mg, 1.4 mmol), the solution temperature was gradually raised from 0° C., and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (20 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (20 ml). The ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml), and once with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: chloroform:methanol=3:1) to give 3-(3-methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-methoxycarbonylethyl]-2-propenamide (413 mg, yield 78.0%) as a powder.

1. temperaturethe solution temperature was gradually raised from 0° C.
2. customThe solvent was removed under reduced pressure, water (20 ml)
3. additionwas added to the residue
4. extractionthe mixture was extracted twice with ethyl acetate (20 ml)
5. washThe ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml)
6. dry with materialonce with saturated brine (5 ml), and dried over anhydrous magnesium sulfate
7. customMagnesium sulfate was removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. custompurified by silica gel column chromatography (eluent: chloroform:methanol=3:1)