Dl-Tryptophan → N-(3-acetoxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide

HRID 128821

Reaktionsgleichung

Reaktionsgleichung von HRID 128821
F[C:2](F)(F)[C:3]([O:5][CH2:6][CH3:7])=[O:4].N[CH:11]([C:22]([OH:24])=O)[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.C([N:27]([CH2:30][CH3:31])CC)C.CN([CH:35]=[O:36])C>>[C:3]([O:5][C:6]1[CH:7]=[C:31]([CH:13]=[CH:12][C:11]=1[C:22]([O:36][CH3:35])=[O:24])[CH2:30][NH:27][C:22](=[O:24])[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)(=[O:4])[CH3:2]

Komponenten

5

Edukt 4

HCID 1148Dl-TryptophanHCID 6228DimethylformamideHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Produkt 1

HCID 10475717N-(3-acetoxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamideAusbeute 50 %

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Ethyl trifluoroacetate (1.7 mL) was added to a stirred solution of DL-tryptophan (2.3 g) and triethylamine (1.6 mL) in DMF (5 mL), then the flask was sealed and purged with nitrogen, and the mixture stirred at 20° C. for 1 day (method of Curphey T. J., J. Org. Chem. 1979;44:2805). Excess reagents were removed under vacuum, then triethylamine (1.9 mL) and DMF (10 mL) were added, and the mixture cooled to 0° C. DEPC (98%, 2.0 mL) was added, followed by benzylamine (1.72 mL), then the mixture was stirred under nitrogen at 20° C. for 1 day. The resulting solution was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). Evaporation gave an oil which was purified by chromatography on silica gel, eluting with EtOAc:light petroleum (1:1), to give DL-N-benzyl-α-trifluoroacetylamino-3-(3-indolyl) propanamide [II: R1 =R3 =H, R2 =CH2CH(NHCOCF3)CONHCH2Ph] (2.21 g, 50%); mp (EtOAc/light petroleum) 181°-183° C.

Aufarbeitung

  1. customthe flask was sealed
  2. custompurged with nitrogen
  3. customExcess reagents were removed under vacuum
  4. additiontriethylamine (1.9 mL) and DMF (10 mL) were added
  5. temperaturethe mixture cooled to 0° C
  6. additionDEPC (98%, 2.0 mL) was added
  7. stirringthe mixture was stirred under nitrogen at 20° C. for 1 day
  8. additionThe resulting solution was diluted with water (100 mL)
  9. extractionextracted with EtOAc (3×100 mL)
  10. customEvaporation
  11. customgave an oil which
  12. customwas purified by chromatography on silica gel
  13. washeluting with EtOAc:light petroleum (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8f9055773d294b50986434dafbcf68f4
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464861

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