Isopropanol → HCID 86740487, compound

HRID 621158Notes

Reaction equation

HRID 621158 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 86740487HCID 86740487, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-99938fa5a8104f9fa6ac3c07d872f5b1
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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