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

HRID 733362Notes

Reaction equation

HRID 733362 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:31][CH3:32])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:16]=2[O:17][CH2:18][C:19]([O:21]CC)=[O:20])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:31][CH3:32])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:16]=2[O:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

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-536d82f38e5a4c4db178c6f78baea124
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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