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Sodium hydride → tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1368639
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1368639
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>O1CCCC1.O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[C:11]([NH:20][S:34]([C:31]2[CH:32]=[CH:33][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 22281904tert-butyl 3-[2-(acetyloxy)ethoxy]-5-amino-1-methyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 22282018tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate
Ausbeute 13,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To tert-butyl 3-[2-(acetyloxy)ethoxy]-5-amino-1-methyl-1H-pyrazole-4-carboxylate (Preparation 10) (70 g) in solution in tetrahydrofuran (1 lit.) at 0° C. was added sodium hydride (20.2 g of a 60% dispersion in oil). The reaction mixture was stirred at room temperature for one hour and then 4-(tert-butyl)benzenesulfonyl chloride (58.88 g) was added dropwise. The reaction mixture was stirred at room temperature overnight and was then diluted with water (200 ml) at 0° C., followed by a saturated solution of ammonium chloride (200 ml) while allowing the mixture to warm to room temperature. The white precipitate was filtered off and disposed of. The aqueous and organic layers were separated and the aqueous extracted with ethyl acetate (100 ml). The combined organics were dried on magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography on a suction column packed with silica eluted with ethyl acetate:hexane (1:4) to yield the desired product as white solid (16 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. temperatureto warm to room temperature
  3. filtrationThe white precipitate was filtered off
  4. customThe aqueous and organic layers were separated
  5. extractionthe aqueous extracted with ethyl acetate (100 ml)
  6. customThe combined organics were dried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was purified by chromatography on a suction column
  10. washeluted with ethyl acetate:hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-86e09a393bf540f1acffb1b425808dea
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06573270B1

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