反应详情

温度

90 °C

Under inert atmosphere and rapid stirring 52 mg of NaOH are pulverized into anhydrous xylene (20 ml), heating the suspension at approximately 90° C. 550 mg of 6-chlorogramine (prepared as described in example 1) and 460 mg of ethyl-acetamido-acetate are then added. The mixture is refluxed for approximately 7 hours and the development of dimethylamine, extremely vigorous at the start of the heating, practically ceases after about 6 hours of heating. The reaction mixture is cooled for 12 hours at 5° C. and then filtered to recover the abundant precipitate. This crude solid is treated with a hot solution of benzene/absolute ethanol, and the insoluble material is hot-filtered. The solution is left to rest at 5° C. for 12 hours. Crystals slowly separate, which are filtered and dried. 750 mg of ethyl-α-acetamido-α-cyano-β-(6-chloro-indole-3-yl)-propioanate are recovered, with a yield of 84%. 600 mg of this compound are added to 15 ml of water, containing 40 mg of NaOH and the mixture is boiled for 24 hours. During this time the solid material dissolves and ammonia is developed. After the reflux time, the reaction mixture is cooled at room temperature and neutralized with acetic acid at 50%. It is filtered, recovering and washing with cold water the solid which has formed. After drying 410 mg of 6-chloro-DL-tryptophan are recovered, with a yield of 95%.

1. temperatureThe mixture is refluxed for approximately 7 hours
2. temperatureof heating
3. temperatureThe reaction mixture is cooled for 12 hours at 5° C.
4. filtrationfiltered
5. customto recover the abundant precipitate
6. additionThis crude solid is treated with a hot solution of benzene/absolute ethanol
7. filtrationthe insoluble material is hot-filtered
8. waitThe solution is left
9. customCrystals slowly separate
10. filtrationwhich are filtered
11. customdried
12. custom750 mg of ethyl-α-acetamido-α-cyano-β-(6-chloro-indole-3-yl)-propioanate are recovered, with a yield of 84%
13. addition600 mg of this compound are added to 15 ml of water
14. additioncontaining 40 mg of NaOH
15. waitthe mixture is boiled for 24 hours
16. dissolutionDuring this time the solid material dissolves
17. temperatureAfter the reflux time, the reaction mixture is cooled at room temperature and neutralized with acetic acid at 50%
18. filtrationIt is filtered
19. customrecovering
20. washwashing with cold water the solid which
21. customhas formed
22. dry with materialAfter drying 410 mg of 6-chloro-DL-tryptophan
23. customare recovered, with a yield of 95%