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Indole → 2-Amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester

HRID 36327
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36327
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH:24](NC(C)C)[CH2:25][O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C2[C:35](=[CH:36]C=CC=2)[CH:34]=C1.[CH3:41][N:42](C)C=O>>[CH:35]([O:2][C:1](=[O:4])[CH:41]([NH2:42])[CH:24]([C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([O:14][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:16]=2)[NH:20][CH:19]=1)[CH2:25][O:26][CH3:27])([CH3:36])[CH3:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 798IndoleHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 14076272HCID 14076272, Verbindung

Produkt 1

HCID 140762742-Amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl esterAusbeute 70 %

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Under nitrogen, 6 g (43.5 millimoles) of finely pulverized potassium carbonate is stirred for 10 minutes at 95° C. in 25 ml of absolute dimethylformamide. Then, while the mixture is hot, 10 g (29.6 mmol) of 5-benzyloxy-3-(1-isopropylamino-2-methoxyethyl)indole is added and the mixture is stirred approximately 10 minutes at 95° C. until the compound has been dissolved. Thereupon, likewise at 95° C., a solution of 34.5 mmol of glycine anisaldehyde isopropyl ester in 25 ml of dimethylformamide is added dropwise in a time period of 30 minutes. The solution is agitated until the starting indole can no longer be detected in a thin-layer chromatogram. After cooling, the product is filtered off by suction from potassium carbonate and rinsed with toluene. After adding 100 ml of toluene, 200 ml of 1N hydrochloric acid is added and the mixture stirred for 3 hours at room temperature. The toluene phase is separated, and the aqueous acidic phase is extracted by shaking with 100 ml of toluene. The organic phase is discarded. The acidic phase is cooled to 5° C., combined with 100 ml of toluene, and adjusted to pH 10-12 with 4N sodium hydroxide solution. After extraction by shaking, the mixture is again extracted by shaking with 100 ml of toluene, and the combined organic phase is washed with 50 ml of water, dried, filtered, and concentrated, thus obtaining 70% 2-amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester as an oil.

Aufarbeitung

  1. dissolutionhas been dissolved
  2. temperatureAfter cooling
  3. filtrationthe product is filtered off by suction from potassium carbonate
  4. washrinsed with toluene
  5. additionAfter adding 100 ml of toluene, 200 ml of 1N hydrochloric acid
  6. additionis added
  7. stirringthe mixture stirred for 3 hours at room temperature
  8. customThe toluene phase is separated
  9. extractionthe aqueous acidic phase is extracted
  10. stirringby shaking with 100 ml of toluene
  11. temperatureThe acidic phase is cooled to 5° C.
  12. extractionAfter extraction
  13. stirringby shaking
  14. extractionthe mixture is again extracted
  15. stirringby shaking with 100 ml of toluene
  16. washthe combined organic phase is washed with 50 ml of water
  17. customdried
  18. filtrationfiltered
  19. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-29756d0be67c4f269bc6542d648ec1e5
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05414002

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