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

HRID 1032353

Reaction equation

HRID 1032353 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-428b98e828e94a269771bea05d804bbe
Source dataset
uspto-grants-1990_09
Patent number
US04957912

Linked notes

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