Trifluoroacetic acid → HCID 86657962, compound

HRID 2366761Notes

Reaction equation

HRID 2366761 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:18]=1)C(=O)OC(C)(C)C>>[F:26][C:25]([F:27])([F:28])[C:24]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([NH:9][CH3:8])[CH:18]=1)=[O:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86657963HCID 86657963, compound

Product 1

HCID 86657962HCID 86657962, compoundYield 89.2%

Procedure

To trifluoroacetic acid (144 mL) was added tert-butyl methyl{3-[(trifluoroacetyl)amino]phenyl}carbamate (47.8 g, 0.150 mol) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate (500 ml) was added to the residue, and the mixture was washed successively with aqueous sodium hydrogen carbonate solution (200 ml) and saturated brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the precipitate was collected by filtration to give the title compound (29.2 g, 89%) as a pale-green powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (500 ml)
  2. additionwas added to the residue
  3. washthe mixture was washed successively with aqueous sodium hydrogen carbonate solution (200 ml) and saturated brine (200 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2621facf971d46d3bc79406c5d439410
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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