Methyl 3-(1H-indol-3-yl)-2-oxopropanoate → HCID 18663409, Verbindung

HRID 1957017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957017
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH3:29])[CH:28]=1)[C:5]([N:7]1[CH:16]([C:17]([CH2:19]P(=O)(OC)OC)=[O:18])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=[O:6].[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:39][C:40](=O)[C:41]([O:43]C)=[O:42])=[CH:31]1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH3:29])[CH:28]=1)[C:5]([N:7]1[CH:16]([C:17]([CH2:19][CH:40]([CH2:39][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:30][CH:31]=2)[C:41]([OH:43])=[O:42])=[O:18])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=[O:6]

Komponenten

4

Edukt 2

HCID 582619Methyl 3-(1H-indol-3-yl)-2-oxopropanoateHCID 18663426HCID 18663426, Verbindung

Produkt 1

HCID 18663409HCID 18663409, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Katalysator

Versuchsvorschrift

A Wittig-Horner reaction according to example 78 between dimethyl N-(3,5-dimethylbenzoyl)-1,2,3,4-tetrahydro-3-isoquinolinecarbonylmethylphosphonate [from methyl N-(3,5-dimethylbenzoyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate (prepared according to example 88) as described in example 78] and methyl 3-indolepyruvate followed by catalytic hydrogenation of the double bond in the presence of Wilkinson's catalyst according to example 78 and hydrolysis of the methyl ester moiety according to example 12 gives 3-[N-(3,5-dimethylbenzoyl)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl]-2-(3-indolyl)methyl-propionic acid as a mixture of isomers; FAB-MS m/e 495 (M+H)+.

Aufarbeitung

  1. customA Wittig-Horner reaction

Quellen und Nachweise

ORD-Eintrag
ord-f785f9c445f94ca8b63e60e15d95a7e0
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780498

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