Toluene → 5-Fluoro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamide

HRID 748498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748498
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:36]=[CH:35][C:12]2[S:13][C:14]([S:17]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([C:25](OC)=[O:26])=[CH:23][C:22]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:19])=[O:18])=[C:15]([CH3:16])[C:11]=2[CH:10]=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)(=O)C.O>[F:8][C:9]1[CH:36]=[CH:35][C:12]2[S:13][C:14]([S:17]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([CH2:25][OH:26])=[CH:23][C:22]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:19])=[O:18])=[C:15]([CH3:16])[C:11]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 1140Toluene2×HCID 9825353Methyl 4-(5-fluoro-3-methylbenzo[b]thiophene-2-sulfonylamino)-3-methanesulfonylbenzoateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 220414435-Fluoro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamideAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

Into 120 mL of toluene was dissolved 2.08 g of Compound 17. After cooling to −30° C., 22.5 mL of 1.01 mol/L toluene solution of diisobutylaluminum hydride was added thereto. After 5 hours of stirring at the same temperature, water was added to the reaction solution to terminate the reaction and then the mixture was diluted with ethyl acetate, followed by addition of saturated aqueous potassium sodium tartrate solution and 30 minutes of stirring at room temperature. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 1.38 g of the title compound as colorless powder.

Aufarbeitung

  1. additionwas added to the reaction solution
  2. customto terminate
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-06b887273d9a42499c40658c35b9c91c
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399781B2

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