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

HRID 851418Notes

Reaction equation

HRID 851418 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+].C[C:52](C)=[O:53]>O.O.CC(C)=O>[CH3:3][C:2]([C@H:18]1[C:19](=[O:33])[NH:20][C@@H:21]1[CH2:22][C:52]([OH:53])=[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 5

HCID 180AcetoneHCID 1061PhosphateHCID 516875Potassium PermanganateHCID 23667635Sodium periodate2×HCID 56623914methyl 2-{(3S,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl}-3-methylbut-2-enoate

Product 1

HCID 56618986{(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl}acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of methyl 2-{(3S,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl}-3-methylbut-2-enoate (72.9 mg) in acetone (2.03 ml) was added a 0.7 M solution of phosphate buffer (pH 6.8, 1.35 ml) at ambient temperature. To the resulting suspension was added dropwise a solution of sodium periodate (86.0 mg) in water (0.594 ml) at ambient temperature. After stirring for 10 minutes, the reaction mixture was added with sodium periodate (117.2 mg) and potassium permanganate (37.5 mg) and stirred at ambient temperature overnight. The resulting mixture was diluted with water-acetone (15 ml-15 ml) and filtered with celite and the filter cake was washed with water-acetone (1:1). The combined filtrates were concentrated in vacuo at 0° C., acidified to pH 1 with 10% aqueous phosphoric acid, and extracted with chloroform. The organic layer was extracted with chilled 10% aqueous sodium bicarbonate (X3). The aqueous extracts were acidified with 3 N hydrochloric acid and reextracted with chloroform (X3). The chloroform extracts were washed with saturated aqueous sodium chloride containing a small amount of 3 N hydrochloric acid, dried over magnesium sulfate, filtered, and evaporated to give {(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl}acetic acid (36.4 mg) as an amorphous solid.

Workup

  1. stirringstirred at ambient temperature overnight
  2. filtrationfiltered with celite
  3. washthe filter cake was washed with water-acetone (1:1)
  4. concentrationThe combined filtrates were concentrated in vacuo at 0° C.
  5. extractionextracted with chloroform
  6. extractionThe organic layer was extracted
  7. temperaturewith chilled 10% aqueous sodium bicarbonate (X3)
  8. washThe chloroform extracts were washed with saturated aqueous sodium chloride containing a small amount of 3 N hydrochloric acid
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-56a4d762c7fe46b0846fb6d55c51fdb4
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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