Trifluoroacetic acid → HCID 59556943, compound

HRID 1967257Notes

Reaction equation

HRID 1967257 reaction equation
C([O:5][CH2:6][CH:7]1[N:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([Cl:20])[CH:13]=2)[C:10](=[O:21])[C:9]([CH3:23])([CH3:22])[C:8]1=[O:24])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>O>[Cl:20][C:14]1[CH:13]=[C:12]([N:11]2[CH:7]([CH2:6][OH:5])[C:8](=[O:24])[C:9]([CH3:22])([CH3:23])[C:10]2=[O:21])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59556946HCID 59556946, compound

Product 1

HCID 59556943HCID 59556943, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-[5-(tert-butoxy methyl)-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl]-2-chlorobenzonitrile (900 mg) was added trifluoroacetic acid (10 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled to 0° C., and neutralized with saturated sodium hydrogen carbonate solution. Water was added to the reaction mixture, 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=4:1→1:4), and recrystallized from hexane-ethyl acetate to give the title compound as colorless crystals (yield: 655 mg, 87%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:4)
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8f4f505909ad4bfd97cb4ab8109353b3
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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