Sulfuric Acid → trans-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

HRID 231229

Reaktionsgleichung

Reaktionsgleichung von HRID 231229
[Si:1]([O:8][CH: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(OCC)(=O)C>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

7

Edukt 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 67788757trans-3-[1-(Tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

Produkt 1

HCID 67789308trans-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24544Mercuric sulfateKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

trans-3-[1-(tert-Butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone (1.2 g) is dissolved in a mixture of tetrahydrofuran (20 ml) and water (2 ml), and mercury sulfate (0.07 g) and concentrated sulfuric acid (catalytic amount) are added, followed by stirring at room temperature for 15 hours. The reaction mixture is poured into a mixture of ethyl acetate (150 ml) and water (100 ml) and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 0.60 g of trans-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

Aufarbeitung

  1. additionare added
  2. customthe organic layer is separated
  3. washwashed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c725bba06420412bae3985d8dd3dcd1b
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845210

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