Hydrochloric Acid → [4-[2-(5-Cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetic acid

HRID 229606Notes

Reaction equation

HRID 229606 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([CH3:37])(=[O:36])=[O:35])[CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:20]=1[OH:27])(=[O:18])=[O:17])C.[OH-].[Na+].Cl>C(O)C>[C:25]([C:23]1[CH:22]=[CH:21][C:20]([OH:27])=[C:19]([S:16]([NH:15][CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34]([CH3:37])(=[O:36])=[O:35])=[CH:8][C:7]=2[O:6][CH2:5][C:4]([OH:38])=[O:3])(=[O:17])=[O:18])[CH:24]=1)#[N:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12149205Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

Product 1

HCID 17856249[4-[2-(5-Cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetic acidYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 154 g of ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]-acetate in 1.23 L of ethanol was added 275 mL of 2 mol/L sodium hydroxide solution under ice-cooling, and the mixture was stirred under ice-cooling for 1.5 hours. To the reaction mixture was added dropwise 275 mL of 2 mol/L hydrochloric acid, and ethanol was removed under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with brine. The solvent was dried over anhydrous magnesium sulfate, and removed under reduced pressure to give 149 g of [4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetic acid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1.5 hours
  3. customwas removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialThe solvent was dried over anhydrous magnesium sulfate
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-40f3724cd3ad4345ba3414a80c146c27
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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