Hydrochloric Acid → [[2-[2-(5-Cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]amino]acetic acid

HRID 1793953Notes

Reaction equation

HRID 1793953 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:31])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[NH:24][CH2:25][C:26]([O:28]CC)=[O:27])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:31])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[NH:24][CH2:25][C:26]([OH:28])=[O:27])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86595216Ethyl [[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]amino]acetate

Product 1

HCID 12096026[[2-[2-(5-Cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]amino]acetic acidYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.65 g of ethyl [[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]amino]acetate in 10 mL of ethanol was added 14 mL of 2 mol/L sodium hydroxide solution at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added 15 mL of 2 mL of hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 1.416 g of [[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]amino]acetic acid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-51bb9c3725244512a1eff7193c2eefd8
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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