L-Tryptophan → 2-[(4-chlorophenyl)formamido]-3-(1H-indol-3-yl)propanoic acid

HRID 2309237

Reaktionsgleichung

Reaktionsgleichung von HRID 2309237
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][CH:2]([CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[C:13]([OH:15])=[O:14])=[O:22])=[CH:19][CH:18]=1

Komponenten

3

Edukt 2

HCID 6305L-TryptophanHCID 85014-Chlorobenzoyl chloride

Produkt 1

HCID 27875262-[(4-chlorophenyl)formamido]-3-(1H-indol-3-yl)propanoic acidAusbeute 79,2 %

Versuchsvorschrift

By using 10 g of L-tryptophane and 9 g of 4-chlorobenzoyl chloride, and a method similar to that described in reference example 6, recrystallized from methanol-water there was obtained 13.3 g of 2-(4-chlorobenzoylamino)-3-(indol-3-yl)propionic acid in the form of colorless needle-like crystals. Melting point: 100°-102° C. [α]D25 -49.3° (C=1, methanol)

Aufarbeitung

  1. customrecrystallized from methanol-water there

Quellen und Nachweise

ORD-Eintrag
ord-6cb5cc7566c5475a81c2b4ea40e7bc08
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04694017

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