Reaktion #318409

ord-cc66650d54a44bf4858200e34e1686f6

Reaktionsgleichung

CCOC(C)=O.O
ethyl acetate water
C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)N[C@@H]1C#C[Si](C)(C)C
Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone
O=S(=O)(O)O
sulfuric acid
O=C([O-])O.[Na+]
sodium hydrogen carbonate
→
CC(=O)[C@H]1NC(=O)[C@H]1C(C)O[Si](C)(C)C(C)(C)C
cis-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
Ausbeute 18.1%

Edukte

CCOC(C)=O.O
ethyl acetate water
C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C(=O)N[C@@H]1C#C[Si](C)(C)C
Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone
O=S(=O)(O)O
sulfuric acid
O=C([O-])O.[Na+]
sodium hydrogen carbonate

Reagenzien

O=S(=O)([O-])[O-].[Hg+2]
mercury sulfate

Lösungsmittel

C1CCOC1
tetrahydrofuran
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONare added
  2. 2
    Sonstigethe organic layer is separated
  3. 3
    Waschenwashed with aqueous sodium chloride
  4. 4
    Trocknendried over magnesium sulfate
  5. 5
    Einengenconcentrated under reduced pressure

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04845210uspto-grants-1989_07