Cesium fluoride → N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamide

HRID 1251791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251791
C[Si](C)(C)CCOC[C:7]1([CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]([S:12]([NH:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[C:17]=2[CH3:22])(=[O:14])=[O:13])[CH:10]=[CH:9][S:8]1.[F-].[Cs+]>CN(C=O)C>[CH3:21][C:18]1[C:17]([CH3:22])=[C:16]([NH:15][S:12]([C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:14])=[O:13])[O:20][N:19]=1

Komponenten

4

Edukt 2

HCID 25953Cesium fluorideHCID 22998524HCID 22998524, Verbindung

Produkt 1

HCID 22998493N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)-2-(α-hydroxybenzyl)thiophene-3-sulfonamide (70 mg, 0-14 mmol) in DMF (2 ml) was added cesium fluoride (26 mg, 0.17 mmole) in one portion. The resulting mixture was heated to 100° C. for 10 hours. The solvents were removed by evaporation under vacuum and the remaining residue was extracted into ethyl acetate, washed with water, brine, and dried over MgSO4. The product was then purified by chromatography using 50-70% ethyl acetate/hexanes to give 26.2 mg N-(3,4-dimethyl-5-isoxazolyl)-2-(α-hydroxybenzyl)thiophene-3-sulfonamide as a pale white semisolid (51% yield).

Aufarbeitung

  1. customThe solvents were removed by evaporation under vacuum
  2. extractionthe remaining residue was extracted into ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe product was then purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-879eba9c82ac47e3981a1911088fc900
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342610B2

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