Dimethylamine → 6-Chloro-L-tryptophan

HRID 248433

反応式

HRID 248433 の反応式
[OH-].[Na+].CN([CH2:6][C:7]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[NH:9][CH:8]=1)C.C([O:19][C:20](=[O:26])[CH2:21][NH:22]C(=O)C)C.CNC>C1(C)C(C)=CC=CC=1>[Cl:16][C:14]1[CH:15]=[C:10]2[C:11](=[CH:12][CH:13]=1)[C:7]([CH2:6][C@@H:21]([C:20]([OH:26])=[O:19])[NH2:22])=[CH:8][NH:9]2

参加物

6

反応物 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 74702Ethyl acetamidoacetateHCID 2458146-Chlorogramine

生成物 1

HCID 100626936-Chloro-L-tryptophan収率 84%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
90 °C

実験手順

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%.

後処理

  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%

出典と根拠

ORDレコード
ord-3a429a1cfe6446f4b65e0ccd93b249bf
出典データセット
uspto-grants-1993_05
特許番号
US05210215

関連ノート

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