Trifluoroacetic acid → HCID 57860101, compound

HRID 1513586Notes

Reaction equation

HRID 1513586 reaction equation
Cl.[CH2:2]([N:4]([CH2:36][CH3:37])[CH2:5][CH2:6][N:7]([CH3:35])[C:8]([C:10]1[S:22][C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14](CC3C=CC(OC)=CC=3)[C:13](=[O:32])[C:12]=2[C:11]=1[O:33][CH3:34])=[O:9])[CH3:3].FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>>[CH2:36]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][N:7]([CH3:35])[C:8]([C:10]1[S:22][C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14][C:13](=[O:32])[C:12]=2[C:11]=1[O:33][CH3:34])=[O:9])[CH3:37]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 66893107HCID 66893107, compound

Product 1

HCID 57860101HCID 57860101, compoundYield 48%

Conditions

Temperature
80 °C

Procedure

A mixture of the compound of Example 48 (4.10 g, 8.08 mol), trifluoroacetic acid (34 mL) and trifluoromethanesulfonic acid (6.6 mL) was stirred at room temperature for 5 hr and at 80° C. for 2.5 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and ethyl acetate and 1N aqueous sodium hydroxide solution were added to the residue. The mixture was extracted with ethyl acetate and the extract was washed successively with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=1/2) to give the title compound (1.50 g, 48%) as a white powder.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and ethyl acetate and 1N aqueous sodium hydroxide solution
  3. additionwere added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-b13bbec0f32a4acc8a45dcd1dfc1e210
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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