Acetic Acid → 2-Azetidinone, 4-(acetyloxy)-3-ethyl-

HRID 1612920Notes

Reaction equation

HRID 1612920 reaction equation
[CH2:1]([CH:3]1[CH2:6][NH:5][C:4]1=[O:7])[CH3:2].[C:8]([O-:11])(=[O:10])[CH3:9].[Na+].C(O)(=O)C.C(OO)(=O)C>C(OCC)(=O)C.O.O.O.[Os](Cl)(Cl)Cl.O>[C:8]([O:11][CH:6]1[NH:5][C:4](=[O:7])[CH:3]1[CH2:1][CH3:2])(=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 190499603-Ethylazetidine-2-one2×

Product 1

HCID 117884382-Azetidinone, 4-(acetyloxy)-3-ethyl-Yield 99.3%

Reagents, catalysts & solvents 3

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

Procedure

To a solution prepared by mixing 500 mg (5 mmole) of 3-ethylazetidin-2-one, 415 mg (5 mmole) of anhydrous sodium acetate, 5 ml of acetic acid, and 30 mg (abut 2 mole % based on the amount of 3-ethylazetidin-2-one) of osmium trichloride trihydrate was added dropwise, with stirring , 2.8 g (11 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 further stirred at room temperature for 4 hours, subsequently poured into 80 ml of water, and then extracted thrice with 100 ml of hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume). Thus, 780 mg of 4-acetoxy-3-ethylazetidin-2-one was obtained. The percent yield was 78%.

Workup

  1. customTo a solution prepared
  2. additionwas added dropwise
  3. stirringThe reaction mixture was further stirred at room temperature for 4 hours
  4. extractionextracted thrice with 100 ml of hexane
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe residue was separated
  8. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume)

Sources & evidence

ORD record
ord-87c16a1c75a1428384c6fc47e701ed4e
Source dataset
uspto-grants-1993_03
Patent number
US05191076

Reaction notes

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