Dicyclohexylcarbodiimide → 5-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-3-(R)-methyl-5-oxo-N-(1-phenylethyl)pentanamide

HRID 2406654Notes

Reaction equation

HRID 2406654 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:5]2[C:18](=[O:26])[CH2:19][C@@H:20]([CH3:25])[CH2:21][C:22](O)=[O:23].[C:27]1([C@H:33]([NH2:35])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1CCC(N=C=NC2CCCCC2)CC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:5]2[C:18](=[O:26])[CH2:19][C@@H:20]([CH3:25])[CH2:21][C:22]([NH:35][CH:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:34])=[O:23]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 6431891-Phenethylamine, (+)-HCID 49802026(3R)-5-(5-chloro-2-hexyl-1-methylindol-3-yl)-3-methyl-5-oxopentanoic acid

Product 1

HCID 498025875-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-3-(R)-methyl-5-oxo-N-(1-phenylethyl)pentanamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 5-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-3-(R)-methyl-5-oxopentanoic acid in methylene chloride was added (R)-1-phenylethanamine followed by the addition of DCC and DMAP and was stirred for 30 minutes. The reaction mixture was treated with sodium bicarbonate and methylene chloride. The product was purified by column chromatography.

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e1d62f99f2d5418c916fd3ff7f643afc
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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