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

HRID 1683496Notes

Reaction equation

HRID 1683496 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-9c47e4afe34844ae82b88d066036c9c6
Source dataset
uspto-grants-1997_06
Patent number
US05637770

Reaction notes

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