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

HRID 1957017Notes

Reaction equation

HRID 1957017 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 18663409HCID 18663409, compound

Reagents, catalysts & solvents 1

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst

Procedure

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)+.

Workup

  1. customA Wittig-Horner reaction

Sources & evidence

ORD record
ord-f785f9c445f94ca8b63e60e15d95a7e0
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

Loading…