tert-Butyl hydroperoxide → 4-(3-Benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

HRID 851380

Reaktionsgleichung

[O:1]=[C:2]1[NH:5][CH:4]([CH2:6][CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C([O:23]O)(C)(C)C>C(O)(=O)C.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl>[O:23]=[C:7]([CH2:6][CH:4]1[CH2:3][C:2](=[O:1])[NH:5]1)[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate (167 mg), tert-butylhydroperoxide (0.3 ml), and sodium tetrachloropalladate (80 mg) in 67% aqueous acetic acid (2.7 ml) was heated at 50° C. for 8.5 hours. Additional tert-butylhydroperoxide (0.5 ml) and sodium tetrachloropalladate (40 mg) were added. The reaction mixture was stirred at room temperature for three days and heated at 50° C. for 14 hours. After evaporation of the solvent in vacuo, the residue was taken up into ethyl acetate (20 ml) and washed with dilute aqueous sodium chloride. Drying over magnesium sulfate and evaporation left an oil (200 mg), which was chromatographed on silica gel plate (developing solvent: 20% acetone in dichloromethane) afforded benzyl 3-oxo-4-[(2RS)-4-oxoazetidin-2-yl]butanoate (66 mg).

Aufarbeitung

temperatureheated at 50° C. for 14 hours
customAfter evaporation of the solvent in vacuo
washwashed with dilute aqueous sodium chloride
dry with materialDrying over magnesium sulfate and evaporation
waitleft an oil (200 mg), which
customwas chromatographed on silica gel plate (developing solvent: 20% acetone in dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-e1a1bbec21e0477989af32a5364604a5
Quelldatensatz: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04383945

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