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

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

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.