Trifluoroacetic acid → HCID 57265837, compound

HRID 1673101Notes

Reaction equation

HRID 1673101 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][C:14]2[C:19]([O:20]COC)=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:11]([F:26])[CH:10]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[Br:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][C:14]2[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:11]([F:26])[CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59715656HCID 59715656, compound

Product 1

HCID 57265837HCID 57265837, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to the compound of Example B244 (134 mg, 0.411 mmol) in methylene chloride (4 ml), and this reaction mixture was stirred at room temperature overnight. After neutralizing the mixture with saturated aqueous sodium hydrogencarbonate, ethyl acetate was added. The ethyl acetate layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (97.5 mg).

Workup

  1. additionwas added
  2. washThe ethyl acetate layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8962d7c56447432faa235a5958f86bd3
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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