Hydrochloric Acid → Androgen receptor modulators 1

HRID 1967387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1967387
[Si](O[C@H]1CC(=O)N([C:15]2[C:16]([C:23]([F:26])([F:25])[F:24])=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[C@H]1CC)(C(C)(C)C)(C)C.[CH2:29]([OH:31])[CH3:30].Cl.[C:33](=[O:36])([O-])O.[Na+]>O1CCCC1>[CH2:17]([C@H:18]1[C@@H:29]([OH:31])[CH2:30][C:33](=[O:36])[N:19]1[C:22]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:23]([F:24])([F:25])[F:26])[CH:15]=1)[CH3:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 86652882((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 59556974Androgen receptor modulators 1Ausbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (7.76 g) in tetrahydrofuran (60 mL)-ethanol (30 mL) was added 6 mol/L hydrochloric acid (60 mL), and the mixture was stirred at room temperature for 18 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/4), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound as a colorless solid (yield: 2.36 g, 42%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/4)
  5. customthe obtained solid was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-862392a7998444cbadffca4504101336
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420694B2

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