Isopropanol → HCID 86740487、化合物

HRID 621158ノート

反応式

HRID 621158 の反応式
C[C:2]1(C)[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:13])[C@H:5]2[N:10]=[N+:11]=[N-:12].CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[N:10]([C@H:5]1[C@H:6]([CH2:7][C:8]([O:9][CH3:2])=[O:17])[NH:3][C:4]1=[O:13])=[N+:11]=[N-:12]

参加物

5

反応物 3

HCID 3776IsopropanolHCID 71403629(6R,7S)-7-Azido-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-oneHCID 131709961Jones' reagent

生成物 1

HCID 86740487HCID 86740487、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

In 30 ml of acetone is dissolved 330 mg of trans-2,2-dimethyl-7-azido-1-aza-3-oxabicyclo[4.2.0]octan-8-one and under ice-cooling and stirring, 3.3 ml (8N solution) of Jones reagent is added. The mixture is stirred for 2.5 hours, after which 5 ml of isopropyl alcohol is added and the mixture is further stirred for 10 minutes. The insolubles are filtered off with the aid of Celite and the filtrate is concentrated under reduced pressure. The residue is shaken with tetrahydrofuran and a small amount of saturated aqueous sodium chloride. The tetrahydrofuran layer is taken and extracted three times with tetrahydrofuran. The tetrahydrofuran layers are combined, dried over anhydrous sodium sulfate and, after additiion of a solution of diazomethane in ether, the mixture is allowed to stand. The solvent is then distilled off and the residue is shaken with water and ethyl acetate. The ethyl acetate layer is taken, washed with aqueous sodium hydrogen carbonate and water in this order and dried over anhydrous sodium sulfate. It is concentrated under reduced pressure and the residue is purified by silica gel column chromatography to give trans-3-azido-4-methoxycarbonylmethyl-2-oxoazetidine.

後処理

  1. temperatureunder ice-cooling
  2. stirringThe mixture is stirred for 2.5 hours
  3. stirringthe mixture is further stirred for 10 minutes
  4. filtrationThe insolubles are filtered off with the aid of Celite
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. stirringThe residue is shaken with tetrahydrofuran
  7. extractionextracted three times with tetrahydrofuran
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. stirringthe residue is shaken with water and ethyl acetate
  11. washwashed with aqueous sodium hydrogen carbonate and water in this order
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationIt is concentrated under reduced pressure
  14. customthe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-99938fa5a8104f9fa6ac3c07d872f5b1
出典データセット
uspto-grants-1989_04
特許番号
US04822788

反応ノート

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