(+-)-5-Hydroxytryptophan → 5-hydroxy-DL-tryptophan methyl ester hydrochloride

HRID 985392

Reaktionsgleichung

Reaktionsgleichung von HRID 985392
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:20]=[C:19]2[C:9]([NH:10][CH:11]=[C:12]2[CH2:13][CH:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:8][CH:7]=1.[CH3:21]O>>[ClH:3].[CH3:21][O:17][C:16](=[O:18])[CH:14]([CH2:13][C:12]1[C:19]2[C:9](=[CH:8][CH:7]=[C:6]([OH:5])[CH:20]=2)[NH:10][CH:11]=1)[NH2:15]

Komponenten

4

Edukt 3

HCID 144(+-)-5-HydroxytryptophanHCID 887MethanolHCID 24386Thionyl Chloride

Produkt 1

HCID 693201345-hydroxy-DL-tryptophan methyl ester hydrochlorideAusbeute 100 %

Versuchsvorschrift

Thionyl chloride (2.14 mL, 29.4 mmol) was added dropwise to a slurry of 5-hydroxy-DL-tryptophan (3.8 g, 17.3 mmol) in anhydrous methanol (40 mL) at 0° C. under a nitrogen blanket. The resulting mixture was warmed slowly to room temperature and stirred for 17 hours. Then the solvent was removed under reduced pressure to provide 5-hydroxy-DL-tryptophan methyl ester hydrochloride (Intermediate 1) as a light brown foam (5.0 g, 100%): 1H NMR (300 MHz, DMSO-d6): δ 10.78 (bs, 1H), 8.62-8.25 (m, 3H), 7.18-7.11 (m, 2H), 6.79 (s, 1H), 6.67-6.61 (m, 1H), 4.18 (m, 1H), 3.69 (s, 3H), 3.25-3.12 (m, 2H).

Aufarbeitung

  1. customThen the solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-02db0697cb5e47ab89af71079f0f892a
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872721B2

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