Trifluoroacetic acid → HCID 59715655, compound

HRID 2078016Notes

Reaction equation

HRID 2078016 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-02ecc8c86bd244d8802ffd3c0255e5d7
Source dataset
uspto-grants-2011_04
Patent number
US07928209B2

Reaction notes

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