Isopropanol → [(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid

HRID 1719345Notes

Reaction equation

HRID 1719345 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[C:9]([CH3:25])([O:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13])[CH3:10].CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:10][C:9]([C@@H:5]1[C:6](=[O:8])[NH:7][C@@H:4]1[CH2:3][C:2]([OH:28])=[O:1])([O:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[O:13])[CH3:25]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 53711022(3R,4R)-4-(2-hydroxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]azetidin-2-oneHCID 131709961Jones' reagent

Product 1

HCID 54113415[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of (3R,4R)-4-(2-hydroxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (50 mg) in acetone (3 ml) was added to a solution of 2N Jones reagent (0.284 ml) in acetone (3 ml) at ambient temperature over a period of 30 minutes and the mixture was stirred for 30 minutes. After addition of an excess of isopropyl alcohol to the mixture, the solvent was evaporated off. The residue was dissolved in chloroform and washed with water. The aqueous layer was extracted twice with chloroform. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in chloroform (5 ml) and the solution was extracted with 0.1N aqueous solution of sodium bicarbonate (2 ml), 0.05N aqueous solution of sodium bicarbonate (2 ml) and water. The aqueous extracts were combined, acidified with 1N hydrochloric acid and extracted three times with chloroform. The combined chloroform extracts were washed with brine, dried over magnesium sulfate and evaporated to give {(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl]-4-oxoazetidin-2-yl}acetic acid (56 mg).

Workup

  1. customthe solvent was evaporated off
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with water
  4. extractionThe aqueous layer was extracted twice with chloroform
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in chloroform (5 ml)
  9. extractionthe solution was extracted with 0.1N aqueous solution of sodium bicarbonate (2 ml), 0.05N aqueous solution of sodium bicarbonate (2 ml) and water
  10. extractionextracted three times with chloroform
  11. washThe combined chloroform extracts were washed with brine
  12. dry with materialdried over magnesium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-127fc4ee11e04555b07f61437ded58a7
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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