Acetic Acid → 4-(2-Acetylamino-4,5-difluorophenyl)butanoic acid

HRID 355971Notes

Reaction equation

HRID 355971 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:4]([N+:15]([O-])=O)[CH:3]=1.[C:18](O)(=[O:20])[CH3:19]>C(OC(=O)C)(=O)C.[Pd]>[C:18]([NH:15][C:4]1[CH:3]=[C:2]([F:1])[C:7]([F:8])=[CH:6][C:5]=1[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22449552HCID 22449552, compound

Product 1

HCID 105872254-(2-Acetylamino-4,5-difluorophenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The compound obtained in (3) above (380 mg) was dissolved in a mixed solvent of 5 ml of acetic acid and 10 ml of acetic anhydride. Upon the addition of 60 mg of 10% palladium-on-carbon, the mixture was catalytically hydrogenated. The catalyst was removed by filtration, the solvent was evaporated, and the residue was subjected to silica gel column chromatography using a chloroform-methanol (10:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 90 mg of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. additionmixed solvent as an eluant
  4. customto obtain fractions
  5. additioncontaining the target compound
  6. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-8716c6249b064c5b8e5f22f4baf36685
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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