Tetrahydrofuran → 3-Benzyloxycarbonylamino-2,2-difluoropropionic acid

HRID 2415645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415645
C[O:2][C:3](=[O:19])[C:4]([F:18])([F:17])[CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1COCC1.[OH-].[Na+]>CO>[CH2:10]([O:9][C:7]([NH:6][CH2:5][C:4]([F:17])([F:18])[C:3]([OH:19])=[O:2])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 235267113-Benzyloxycarbonylamino-2,2-difluoropropionic acid methyl ester

Produkt 1

HCID 226353073-Benzyloxycarbonylamino-2,2-difluoropropionic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Benzyloxycarbonylamino-2,2-difluoropropionic acid methyl ester (3.3 g, 12.1 mmol), THF (50 ml), methanol (50 ml) and 1 N sodium hydroxide solution (50ml) were mixed and stirred for 16 hours at room temperature. After adjusting the pH to acidic reaction and removal of organic solvent by evaporation, the aqueous residue was extracted twice with ethyl acetate. The combined organic layers were washed twice with 5% brine, dried over magnesium sulphate and filtered through a short silica column before concentration in vacuo to afford 2.6 g (83%) of 3-benzyloxycarbonylamino-2,2-difluoropropionic acid as an oil.

Aufarbeitung

  1. customto acidic reaction and removal of organic solvent
  2. customby evaporation
  3. extractionthe aqueous residue was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed twice with 5% brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered through a short silica column before concentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c88b25d4c7b74ea691ee76bf8da6acd5
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821960B2

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