Potassium Hydroxide → 3,3-Dimethyl-5-oxo-5-(2-undecyl-indol-1-yl)-pentanoic acid

HRID 2406648Notes

Reaction equation

HRID 2406648 reaction equation
[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH-].[K+].[CH3:23][C:24]1([CH3:32])[CH2:29][C:28](=[O:30])[O:27][C:26](=[O:31])[CH2:25]1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH3:23][C:24]([CH3:32])([CH2:29][C:28](=[O:30])[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[C:12]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:25][C:26]([OH:31])=[O:27]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 778133,3-Dimethylglutaric anhydrideHCID 687508802-undecyl-1H-indole

Product 1

HCID 498005593,3-Dimethyl-5-oxo-5-(2-undecyl-indol-1-yl)-pentanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-undecyl-1H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture 4,4-dimethyl-dihydro-pyran-2,6-dione was added and stirred for 3 hours. The reaction mixture was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-576b7a9c700146ae9ce0ab4a8c550c10
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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