Sodium Hydroxide → [2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid

HRID 1272422Notes

Reaction equation

HRID 1272422 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=1[O:30][CH3:31])(=[O:21])=[O:20])C.[OH-].[Na+]>C(O)C>[C:28]([C:26]1[CH:25]=[CH:24][C:23]([O:30][CH3:31])=[C:22]([S:19]([NH:18][CH2:17][CH2:16][C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:15])[CH3:14])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:32])=[O:3])(=[O:20])=[O:21])[CH:27]=1)#[N:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17856206Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

Product 1

HCID 18456942[2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.52 g of ethyl[2-[2-(5-cyano-2-methoxy-benzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate in ethanol was added 12.3 mL of 2 mol/L sodium hydroxide solution to neutralize. After being stirred at room temperature for 3 hours, the reaction mixture was concentrated, and 1 mol/L hydrochloric acid was added to the residue. After the mixture was extracted with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4.16 g of [2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. addition1 mol/L hydrochloric acid was added to the residue
  3. extractionAfter the mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-145c644886ed40fa9458a06d4d577623
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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