Hydrogen Peroxide → HCID 46181191, compound

HRID 2280324Notes

Reaction equation

HRID 2280324 reaction equation
[OH:1]O.[OH-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:17][CH:16]=[C:15]2[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:9]=[CH:10][C:11]=1[C:12]#[N:13]>CO>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:17][CH:16]=[C:15]2[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:7][C:6]=1[Cl:5])(=[O:1])[NH2:13]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 58305635HCID 58305635, compound

Product 1

HCID 46181191HCID 46181191, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An 8 ml vial was loaded with a mixture of 30% H2O2 (50 uL), 3N NaOH (0.15 ml) and MeOH (0.125 ml). To this mixture 3-[1-(3-chloro-4-cyanophenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl]propanoic acid (40 mg, 0.105 mmol) was added at room temperature. The reaction mixture was stirred at rt for 45 minutes, TLC showed the starting material to be consumed. The reaction mixture was diluted with water, acidified to pH=2, stirred for 10 minutes, and filtered off. The solid was washed with water and dried to give 30 mg of 3-(1-(4-carbamoyl-3-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoic acid, 73% yield.

Workup

  1. customto be consumed
  2. additionThe reaction mixture was diluted with water
  3. stirringstirred for 10 minutes
  4. filtrationfiltered off
  5. washThe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-f06ca13c290b4a2f83e053e4af4ac24e
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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