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

HRID 354548

Reaktionsgleichung

Reaktionsgleichung von HRID 354548
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 205083403-Boc-amino-4-fluorobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2e148432ad554c87b2a391b53bd66daf
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04375477

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