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

HRID 1272437
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1272437
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 17856249[4-[2-(5-Cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetic acidAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel
2×

Versuchsvorschrift

To a stirred solution of 154 g of ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonyl-biphenyl-3-yloxy]acetate in 1.23 L of ethanol was added 275 mL of 2mol/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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a2261578fbe6455d91d402c6aac4162a
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07208524B2

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