Trifluoroacetic acid → HCID 57860101, compound

HRID 1947132Notes

Reaction equation

HRID 1947132 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-21bcff0c1feb4858b28ba40f2964382f
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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