Acetic Acid → 3-Boc-amino-4-fluorobutanoic acid

Reaction equation

[F:1][CH2:2][CH:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])CC=C.[Mn]([O-])(=O)(=O)=O.[K+].[C:21]([OH:24])(=[O:23])[CH3:22]>O>[F:1][CH2:2][CH:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:22][C:21]([OH:24])=[O:23]

Participants

Procedure

1-Fluoro-2-tert-butoxycarbonylamino-4-pentene (1.02 g, 5 mmoles), dissolved in glacial acetic acid (15 ml), is added to potassium permanganate (2.37 g, 15 mmoles) in water (75 ml), and kept overnight at room temperature. After destroying the excess of permanganate with 10% sodium bisulfite solution and saturating with sodium chloride, the mixture is extracted twice with ether. Evaporation gives 4-fluoro-3-tert-butoxycarbonylamino-1-butanoic acid (776 mg) as a white solid which on recrystallization from ether/petroleum ether affords 676 mg (61%) of pure material, m.p. 112°-112.5° C.