Benzenepropanal → N-(2-{2-[1-(5-Benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-3-phenyl-propyl]-1H-indol-3-yl}-ethyl)-acetamide

HRID 1432463Notes

Reaction equation

HRID 1432463 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[CH:10]=[C:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH2:21][CH2:22][CH:23]=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])=[CH:26]1>>[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[C:10]([CH:23]([C:26]2[NH:25][C:33]3[C:28]([C:27]=2[CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7707BenzenepropanalHCID 70547N-AcetyltryptamineHCID 690635555-benzyl-4-hydroxy-5H-furan-2-one

Product 1

HCID 57933459N-(2-{2-[1-(5-Benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-3-phenyl-propyl]-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 5-benzyl-4-hydroxy-5H-furan-2-one (Lit. 13) was reacted with 3-phenyl-propionaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide) to give the title compound as a yellow solid. MS: 507.2 ([M−H]−).

Sources & evidence

ORD record
ord-0f6946673b1b45daaaeaceb9b1272008
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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