Acetic Acid → 4-Acetoxy-2-azetidinone

HRID 1612919Notes

Reaction equation

HRID 1612919 reaction equation
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].[C:6]([O-:9])(=[O:8])[CH3:7].[Na+].C(O)(=O)C.C(OO)(=O)C>C(OCC)(=O)C.O.O.O.[Os](Cl)(Cl)Cl.O>[C:6]([O:9][CH:4]1[NH:1][C:2](=[O:5])[CH2:3]1)(=[O:8])[CH3:7]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6585Peracetic AcidHCID 1367212-Azetidinone2×HCID 517045Sodium Acetate

Product 1

HCID 1199814-Acetoxy-2-azetidinoneYield 78.6%

Reagents, catalysts & solvents 3

HCID 57348105Trichloroosmium--water (1/3)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 200 mg (2.8 mmole) of azetidin-2-one, 230 mg (2.8 mmole) of anhydrous sodium acetate, 2 ml of acetic acid, and 17 mg (2 mole % based on the amount of azetidin-2-one) of osmium trichloride trihydrate was added dropwise, with stirring, 1.56 g (6.2 mmole) of a 30% peracetic acid solution in ethyl acetate at room temperature over a period of 2 hours or more. The reaction mixture was poured into 50 ml of water and extracted with n-hexane. The extract was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume). Thus, 280 mg (2.2 mmole, percent yield: 78%) of 4-acetoxyazetidin-2-one in a colorless oily state was obtained.

Workup

  1. additionwas added dropwise
  2. extractionextracted with n-hexane
  3. customThe extract was separated
  4. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume)

Sources & evidence

ORD record
ord-de9a6296fadd4eaebc11e1bdd66e2e6b
Source dataset
uspto-grants-1993_03
Patent number
US05191076

Reaction notes

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