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

HRID 1032353

반응식

HRID 1032353 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-428b98e828e94a269771bea05d804bbe
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957912

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