Potassium Hydroxide → 5-[5-Chloro-2-(5-methyl-hexyl)-indol-1-yl]-3-methyl-5-oxo-pentanoic acid

HRID 2406679Notes

Reaction equation

HRID 2406679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:5]2.[OH-].[K+].[CH3:20][CH:21]1[CH2:26][C:25](=[O:27])[O:24][C:23](=[O:28])[CH2:22]1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:25](=[O:27])[CH2:26][CH:21]([CH3:20])[CH2:22][C:23]([OH:28])=[O:24])[C:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:5]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 778283-Methylglutaric anhydrideHCID 687469275-chloro-2-(5-methyl-hexyl)-1H-indole

Product 1

HCID 666469615-[5-Chloro-2-(5-methyl-hexyl)-indol-1-yl]-3-methyl-5-oxo-pentanoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of 5-chloro-2-(5-methyl-hexyl)-1H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture, 4-methyl-dihydro-pyran-2,6-dione was added and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-47ae22176cfd49e08dbcbaa8486fadb8
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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