Hydrogen Peroxide → HCID 24755545, compound

HRID 1869804Notes

Reaction equation

HRID 1869804 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([O:6][CH:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8]([O:10]C)=[O:9])=[O:5].[Li+].[OH-].OO.OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:3]=1[C:4]([O:6][CH:7]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH:17]=[CH:16]2)[C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 57987631HCID 57987631, compound

Product 1

HCID 24755545HCID 24755545, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{[2-(2,6-dichlorophenyl)-6-quinolinyl]methyl}-2-methoxy-2-oxoethyl 2,6-dichlorobenzoate 57 (0.113 g) in 10 ml THF are added, at 0° C., 1 ml of LiOH (1 M) and 0.5 ml of H2O2 (30%). The solution is then stirred at room temperature for 18 h. After addition of 10 ml KHSO4 (10%), the THF is evaporated. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with brine, dried over MgSO4 and evaporated under vacuum. The residue is triturated in pentane to give 2[(2,6-dichlorobenzoyl)oxy]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid 93 as a white powder.

Workup

  1. customthe THF is evaporated
  2. extractionThe aqueous phase is extracted with AcOEt (3×10 ml)
  3. washThe organic phases are washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum
  6. customThe residue is triturated in pentane

Sources & evidence

ORD record
ord-1a0bd67d31b04075863f41cb050523b4
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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