N-Bromoacetamide → 1-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-methylsulfonyl-2-azetidinone

HRID 903189

Reaktionsgleichung

Reaktionsgleichung von HRID 903189
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[CH:23](SC)[CH:22]([N:26]=[N+:27]=[N-:28])[C:21]1=[O:29])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN[C:32](=O)C.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].[Cl-].[Na+]>CO>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[CH:23]([S:35]([CH3:32])(=[O:39])=[O:37])[CH:22]([N:26]=[N+:27]=[N-:28])[C:21]1=[O:29])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 4353N-BromoacetamideHCID 5234Sodium ChlorideHCID 24477Sodium ThiosulfateHCID 867372521-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-(methylthio)-2-azetidinone

Produkt 1

HCID 867372511-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-methylsulfonyl-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(Benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-(methylthio)-2-azetidinone (0.44 g.) is dissolved in methanol (20 ml.) and treated with N-bromoacetamide (0.52 g.) for two hours. Sodium thiosulfate (10 ml.; 0.1N) is then added and the mixture is allowed to stir for five minutes. At the end of this time, the reaction mixture shows no positive reaction to starch iodide paper. The reaction mixture is saturated with sodium chloride and extracted with methylene chloride. The methylene chloride extract is dried and evaporated. The residue is chromatographed to afford 1-(benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-methylsulfonyl-2-azetidinone.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. customis dried
  4. customevaporated
  5. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-48b00369a8754112b546bede706d65a9
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04226866

Verknüpfte Notizen

Wird geladen…