Reaktionsgleichung
[Si:1]([O:8][C@@H:9]([C@H:11]1[C@@H:14]([C:15]#[C:16][Si](C)(C)C)[NH:13][C:12]1=[O:21])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:23].C(=O)([O-])O.[Na+].C(OCC)(=O)C.O>O1CCCC1.O.S([O-])([O-])(=O)=O.[Hg+2]>[C:15]([C@H:14]1[NH:13][C:12](=[O:21])[C@H:11]1[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:10])(=[O:23])[CH3:16]Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone (0.24 g) is dissolved in a mixture of tetrahydrofuran (5 ml) and water (1 ml), and mercury sulfate (0.03 g) and concentrated sulfuric acid (0.06 g) are added, followed by stirring at room temperature for 15 hours. After addition of sodium hydrogen carbonate (0.2 g), the reaction mixture is poured into ethyl acetate-water, and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography to give 0.03 g of cis-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.
Aufarbeitung
- additionare added
- customthe organic layer is separated
- washwashed with aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-cc66650d54a44bf4858200e34e1686f6
- Quelldatensatz
- uspto-grants-1989_07
- Patentnummer
- US04845210
Verknüpfte Notizen
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