Water → 2-methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester

HRID 914344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914344
[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:22])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17]S(C)(=O)=O)[N:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]([F:39])([F:38])[C:26]1[CH:27]=[C:28]([N:32]2[CH:36]=[C:35](O)[CH:34]=[N:33]2)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:8])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:35]2[CH:34]=[N:33][N:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:38])([F:39])[F:24])[CH:27]=3)[CH:36]=2)[N:14]=1)[CH3:22])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27830311-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-olHCID 597592982-Methyl-2-[(4-{2-[(methylsulfonyl)oxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester

Produkt 1

HCID 597588922-methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl esterAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2-Methyl-2-[(4-{2-[(methylsulfonyl)oxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester (1.0 g) synthesized in Example 5 and 1-[3-(trifluoromethyl)phenyl]-1H-pyrazole-4-ol (600 mg) were dissolved in N,N-dimethylformamide (10 mL), potassium carbonate (363 mg) was added, and the mixture was stirred at 85° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 4:1) to give the title compound (400 mg) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f80c090d5a2447e683b3f25180a08b06
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

Notizen zur Reaktion

Wird geladen…