Peracetic Acid → 4-Acetoxy-2-azetidinone

HRID 1590775Notes

Reaction equation

HRID 1590775 reaction equation
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].[C:6]([O-:9])(=[O:8])[CH3:7].[Na+].C(OO)(=O)C>[Ru](Br)Br.C1C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[C:6]([O:9][CH:4]1[NH:1][C:2](=[O:5])[CH2:3]1)(=[O:8])[CH3:7]

Participants

7

Reactant 3

HCID 6585Peracetic AcidHCID 1367212-AzetidinoneHCID 517045Sodium Acetate

Product 1

HCID 1199814-Acetoxy-2-azetidinoneYield 65%

Reagents, catalysts & solvents 3

HCID 86746743HCID 86746743, compoundCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.42 g (20 mmol) of azetidine-2-one was added with 1.81 g (22 mmol) of anhydrous sodium acetate, 6.4 g of acetic acid, 5.6 g of ethyl acetate and 0.678 g (2 mmol) of benzene ruthenium dibromide, cooled to 5°-10° C., then added dropwise with 16.5 g of acetic acid solution containing 22% peracetic acid over 1.5 hours while stirring. After the dropping, a further 15 hour stirring was conducted at the same temperature. The solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (hexane/ethyl acetate=1/1 by volume) to obtain 1.67 g of 4-acetoxyazetidine-2-one (yield: 65%).

Workup

  1. temperaturecooled to 5°-10° C.
  2. stirringAfter the dropping, a further 15 hour stirring
  3. distillationThe solvent was distilled off under reduced pressure
  4. customfollowed by purification by silica gel column chromatography (hexane/ethyl acetate=1/1 by volume)

Sources & evidence

ORD record
ord-493d600f612e49d1955a1c1fe7fd31e5
Source dataset
uspto-grants-1993_04
Patent number
US05204460

Reaction notes

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