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

HRID 354548

Reaction equation

HRID 354548 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

5

Reactant 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 20508337N-Boc-1-fluoropent-4-EN-2-amine

Product 1

HCID 205083403-Boc-amino-4-fluorobutanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. customAfter destroying the excess of permanganate with 10% sodium bisulfite solution
  2. concentrationsaturating with sodium chloride
  3. extractionthe mixture is extracted twice with ether
  4. customEvaporation

Sources & evidence

ORD record
ord-2e148432ad554c87b2a391b53bd66daf
Source dataset
uspto-grants-1983_03
Patent number
US04375477

Linked notes

Loading…