Sodium Iodide → cis-3-Azido-4-oxo-2-azetidinylmethyl iodide

HRID 1112343ノート

反応式

HRID 1112343 の反応式
S(C1C=CC(C)=CC=1)(O[CH2:5][C@H:6]1[C@@H:9]([N:10]=[N+:11]=[N-:12])[C:8](=[O:13])[NH:7]1)(=O)=O.[Na+].[I-:22]>CC(C)=O>[N:10]([C@H:9]1[C:8](=[O:13])[NH:7][C@H:6]1[CH2:5][I:22])=[N+:11]=[N-:12]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 86734335HCID 86734335、化合物

生成物 1

HCID 86736077cis-3-Azido-4-oxo-2-azetidinylmethyl iodide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A degassed solution of cis-3-azido-4-oxo-2-azetidinylmethyl tosylate (2.36 g) in acetone (80 ml) was refluxed with NaI (5.85 g) overnight. Reaction was cooled and the acetone was removed in vacuo. The reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulfate solution. Phases were separated and the organic layer was extracted with thiosulfate solution. The combined aqueous extracts were extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried and evaporated to give an off-white solid. The product was recrystallized from ethyl acetate-hexane, melting point 130°-2° (dec.), 1.5 g (75%).

後処理

  1. customReaction
  2. temperaturewas cooled
  3. customthe acetone was removed in vacuo
  4. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulfate solution
  5. customPhases were separated
  6. extractionthe organic layer was extracted with thiosulfate solution
  7. extractionThe combined aqueous extracts were extracted with ethyl acetate
  8. washThe combined ethyl acetate layers were washed with brine
  9. customdried
  10. customevaporated
  11. customto give an off-white solid
  12. customThe product was recrystallized from ethyl acetate-hexane, melting point 130°-2° (dec.), 1.5 g (75%)

出典と根拠

ORDレコード
ord-1816e72e44dc498fadd6fba1a9ab65bc
出典データセット
uspto-grants-1978_10
特許番号
US04122086

反応ノート

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