Hydrochloric Acid → HCID 59556879, compound

HRID 1967367Notes

Reaction equation

HRID 1967367 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.[C:14](=[O:17])([O-])O.[Na+].[CH3:19][OH:20]>C1COCC1>[OH:20][C@H:19]1[C@H:5]([CH3:4])[N:6]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:10]=2)[C:14](=[O:17])[C:3]1([CH3:10])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 679722-(Trifluoromethyl)benzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 59556879HCID 59556879, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)]-2-(trifluoromethyl)benzonitrile (391.7 mg) in THF (12 mL) and methanol (12 mL) was added 6 mol/L hydrochloric acid (12.0 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was added to saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/3) to give the title compound as a colorless oil (yield: 203.6 mg, 66%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/3)

Sources & evidence

ORD record
ord-17ce0fdb26c140febf0bcefcd11b891f
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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