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

HRID 1032353

反応式

HRID 1032353 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-428b98e828e94a269771bea05d804bbe
出典データセット
uspto-grants-1990_09
特許番号
US04957912

関連ノート

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