Sodium Hydroxide → HCID 57987630, compound

HRID 1869802Notes

Reaction equation

HRID 1869802 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[CH2:4][O:5][CH:6]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:7]([O:9]C)=[O:8].[OH-].[Na+].OS([O-])(=O)=O.[K+]>C(#N)C.O>[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[CH2:4][O:5][CH:6]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 57987621HCID 57987621, compound

Product 1

HCID 57987630HCID 57987630, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of methyl 2-[(2,6-dichlorobenzyl)oxy]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 56 (0.123 g) and 1 N NaOH (0.236 ml) in a mixture of acetonitrile/water (3 ml/0.14 ml) is stirred for 3 h at room temperature. After addition of a 10% KHSO4 solution (3 ml), the mixture is concentrated. 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 washed with CH2Cl2 and 2-[(2,6-dichlorobenzyl)oxy]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid 91 is obtained as a white powder.

Workup

  1. concentrationthe mixture is concentrated
  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. washThe residue is washed with CH2Cl2

Sources & evidence

ORD record
ord-04a8c697a0a44d1397843968b61c6f74
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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