tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate → D-tryptophanamide

HRID 2201109

Reaktionsgleichung

Reaktionsgleichung von HRID 2201109
[NH2:1][C:2](=[O:22])[C@H:3]([NH:14]C(=O)OC(C)(C)C)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1>Cl.O1CCOCC1>[NH2:14][C@H:3]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[C:2]([NH2:1])=[O:22]

Komponenten

4

Edukt 1

HCID 57107549tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate

Produkt 1

HCID 688582D-tryptophanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of (R)-tert-butyl 1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate (0.963 g, 3.18 mmol) in 4N HCl in dioxane (8 mL) was stirred at room temperature for 1 h. It was then concentrated in vacuo. The residue was partitioned between nBuOH and aq. 5% NaHCO3. The nBuOH phase was separated, washed with water, concentrated in vacuo to give (R)-2-amino-3-(1H-indol-3-yl)propanamide as free base (0.324 g).

Aufarbeitung

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was partitioned between nBuOH and aq. 5% NaHCO3
  3. customThe nBuOH phase was separated
  4. washwashed with water
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d5cc52ab9ea44a97af10290ad8d4ef7a
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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