Hydrochloric Acid → Androgen receptor modulators 1

HRID 1967387Notes

Reaction equation

HRID 1967387 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 59556974Androgen receptor modulators 1Yield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-862392a7998444cbadffca4504101336
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

Loading…