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

HRID 1719346Notes

Reaction equation

HRID 1719346 reaction equation
[CH3:1][C:2]([C@H:18]1[C@@H:21]([CH2:22]C=C)[N:20](C(=C(C)C)C(OC)=O)[C:19]1=[O:33])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6])[CH3:3].P([O-])([O-])([O-])=O.I([O-])(=O)(=O)=O.[Na+].[Mn]([O-])(=O)(=O)=[O:46].[K+].Cl.C[C:53](C)=[O:54]>O>[CH3:3][C:2]([C@@H:18]1[C:19](=[O:33])[NH:20][C@@H:21]1[CH2:22][C:53]([OH:54])=[O:46])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)=[O:6])[CH3:1]

Participants

8

Reactant 6

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 1061PhosphateHCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 54291793HCID 54291793, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-{(3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-(prop-2-enyl)azetidin-1-yl}-3-methylbut-2-enoate (50 mg) in acetone (2.79 ml) were added water (0.93 ml) and a 0.7M solution of phosphate buffer (pH 6.8, 1.86 ml) at ambient temperature. Sodium periodate (139 mg) was added to the resulting suspension at ambient temperature and the mixture was stirred for 20 minutes. Potassium permanganate (26 mg) was then added and the resulting mixture was stirred for 26 hours at ambient temperature. The mixture was acidified with 2N hydrochloric acid (2 ml) and filtered using diatomaceous earth, and the filter-cake was washed with acetone and water. The filtrates were combined and concentrated under reduced pressure to a half volume. The concentrate was extracted three times with chloroform. The organic layers were combined, washed with brine and extracted with 5% aqueous sodium bicarbonate and water. The combined aqueous extracts were acidified with 2N hydrochloric acid and extracted three times with chloroform. The organic extracts were combined, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give {(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl}acetic acid (16 mg).

Workup

  1. customat ambient temperature
  2. stirringthe resulting mixture was stirred for 26 hours at ambient temperature
  3. filtrationfiltered
  4. washthe filter-cake was washed with acetone and water
  5. concentrationconcentrated under reduced pressure to a half volume
  6. extractionThe concentrate was extracted three times with chloroform
  7. washwashed with brine
  8. extractionextracted with 5% aqueous sodium bicarbonate and water
  9. extractionextracted three times with chloroform
  10. washwashed with brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-146920f4a588428dbd2ea137f841cc1b
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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