Hydrogen Peroxide → HCID 46179380, compound

HRID 238401Notes

Reaction equation

HRID 238401 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH:22]([CH3:27])[CH2:23][C:24]([OH:26])=[O:25])[CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([CH3:28])[CH:4]=1)#[N:2].[OH-:29].[Na+].OO>CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH:22]([CH3:27])[CH2:23][C:24]([OH:26])=[O:25])[CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([CH3:28])[CH:4]=1)(=[O:29])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67176238HCID 67176238, compound

Product 1

HCID 46179380HCID 46179380, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of the crude 3-(2-(4-cyano-2-methylphenyl)-3-(4-methoxyphenyl)-1H-pyrrol-1-yl)butanoic acid (120 mg) in DMSO (5 mL) was added a solution NaOH (26 mg, 0.65 mmol) in a mixture of water (0.5 mL) and H2O2 (0.33 mmol). After being stirred at room temperature for 2 hours, the mixture was purified by preparative HPLC to give 26 mg of 3-(2-(4-carbamoyl-2-methylphenyl)-3-(4-methoxyphenyl)-1H-pyrrol-1-yl)butanoic acid (yield 20% in two steps) as a grey solid.

Workup

  1. customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-3d0a8f9412744221b65663ea2feac30b
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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