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

HRID 851384

Reaktionsgleichung

[Si]([N:8]1[C:11](=[O:12])[CH2:10][CH:9]1[CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(C(C)(C)C)(C)C.C([O:30]O)(C)(C)C>C(O)(=O)C.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl>[O:30]=[C:14]([CH2:13][CH:9]1[CH2:10][C:11](=[O:12])[NH:8]1)[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

To a solution of benzyl 4-[(2RS)-1-(tert-butyl-dimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (50 mg) in 60% aqueous acetic acid (1.5 ml) were added tert-butyl-hydroperoxide (40 μl) and sodium tetrachloropalladate (18 mg). The solution was heated at 55° C. for 5.5 hours. Additional tert-butyl-hydroperoxide (100 μl) and sodium tetrachloropalladate (18 mg) were added and stirring at 50° C. was continued for further 11 hours. After evaporation of the solvent in vacuo, the residue was taken up into ethyl acetate and washed in turn with water (twice) and brine. Drying over magnesium sulfate and removal of the solvent left an oil (30 mg) which was chromatographed on a silica gel plate (developing solvent: 25% acetone in benzene) afforded benzyl 3-oxo-4-[(2RS)-4-oxoazetidin-2-yl]butanoate (13 mg).

Aufarbeitung

customAfter evaporation of the solvent in vacuo
washwashed in turn with water (twice) and brine
dry with materialDrying over magnesium sulfate and removal of the solvent
waitleft an oil (30 mg) which
customwas chromatographed on a silica gel plate (developing solvent: 25% acetone in benzene)

Quellen und Nachweise

ORD-Eintrag: ord-ffaf633080cd4bae8aac0d6761627650
Quelldatensatz: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04383945

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