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

HRID 1432460Notes

Reaction equation

HRID 1432460 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.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])=[CH:16]1>>[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[C:10]([CH:8]([C:16]2[NH:15][C:23]3[C:18]([C:17]=2[CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:1][CH:2]([CH3:7])[CH3:3])=[C:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

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

Product 1

HCID 57933434N-(2-{2-[1-(5-Benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-3-methyl-butyl]-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-methyl-butyraldehydeand and N-[2-(1H-indol-3-yl)-ethyl]-acetamide) to give the title compound as a yellow solid. MS: 459.1 ([M−H ]−).

Sources & evidence

ORD record
ord-4aa6bda5f28d4d51950f0da8a65c3597
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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