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

HRID 1590773Notes

Reaction equation

HRID 1590773 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(Cl)Cl>[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

6

Reactant 4

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

Product 1

HCID 117884382-Azetidinone, 4-(acetyloxy)-3-ethyl-Yield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

1.0 g of 3-ethylazetidine-2-one and 0.83 of anhydrous sodium acetate were suspended in 20 ml of methylene chloride and cooled to -5° C., to which 0.35 g of ruthenium acetylacetonate complex was added. 3.8 ml of acetic acid solution containing 40% peracetic acid was dropped thereto carefully so as to maintain the temperature not higher than 0° C., followed by the procedures in Example 2 to obtain 1.17 g of the title compound (yield: 74.5%).

Workup

  1. additionwas added
  2. additionwas dropped
  3. temperaturecarefully so as to maintain the temperature not higher than 0° C.

Sources & evidence

ORD record
ord-ca63a24464564e00805c2c6a00fcf185
Source dataset
uspto-grants-1993_04
Patent number
US05204460

Reaction notes

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