Trifluoroacetic acid → HCID 59715655, compound

HRID 1673098Notes

Reaction equation

HRID 1673098 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:12]1[CH:28]=[CH:27][C:15]([CH2:16][C:17]2[C:22]([O:23]COC)=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH2:8]([C:12]1[CH:28]=[CH:27][C:15]([CH2:16][C:17]2[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 57712181HCID 57712181, compound

Product 1

HCID 59715655HCID 59715655, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of the compound of Example B229 (256 mg, 0.849 mmol) in methylene chloride (5 ml), and this reaction mixture was stirred at room temperature overnight. After a saturated aqueous sodium hydrogencarbonate solution and ethyl acetate were added, the reaction mixture was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (182 mg).

Workup

  1. washthe reaction mixture was washed with saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-210ca8d97b0f456d9f7432cc5c07b96f
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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