Peracetic Acid → 4-Acetoxy-2-azetidinone

HRID 1590776

Reaktionsgleichung

Reaktionsgleichung von HRID 1590776
C([CH:4]1[NH:7][C:6](=[O:8])[CH2:5]1)(O)=O.[C:9]([O-:12])(=[O:11])[CH3:10].[Na+].C(OO)(=O)C>[Ru](I)I.C1C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[C:9]([O:12][CH:4]1[NH:7][C:6](=[O:8])[CH2:5]1)(=[O:11])[CH3:10]

Komponenten

7

Edukt 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 34880644-Oxoazetidine-2-carboxylic acid

Produkt 1

HCID 1199814-Acetoxy-2-azetidinoneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 86746744Benzene ruthenium diiodideKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.15 g (10 mmol) of 4-carboxyazetidine-2-one (MW 115) was added with 0.905 g (11 mmol) of anhydrous sodium acetate, 3.2 g of acetic acid, 2.8 g of ethyl acetate and 0.433 g (1 mmol) of benzene ruthenium diiodide, cooled to 10°-15° C., then added dropwise 8.25 g of acetic acid solution containing 22% peracetic acid over one hour while stirring. A further 15 hour stirring was carried out 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 0.45 g of 4-acetoxyazetidine-2-one (yield: 35%).

Aufarbeitung

  1. temperaturecooled to 10°-15° C.
  2. stirringA 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)

Quellen und Nachweise

ORD-Eintrag
ord-e17518837c43418ea90283faf1615b8a
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204460

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