Clavulanic Acid → HCID 22807221, Verbindung

HRID 1649172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649172
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6](C(O)=O)/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9]O>C(OCC1C=CC=CC=1)(=O)C=C>[CH:8]([C:7]1[O:11][C@H:2]2[N:3]([C:4](=[O:5])[CH2:1]2)[CH:6]=1)=[CH2:9]

Komponenten

3

Edukt 1

HCID 5280980Clavulanic Acid

Produkt 1

HCID 22807221HCID 22807221, VerbindungAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 75617Benzyl acrylateLösungsmittel

Versuchsvorschrift

(5R)-3-Vinyl-7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene (345 mg., 2.5 mmole) was prepared from clavulanic acid (3.0 mmole) as described in Example 1. This diene was dissolved in benzyl acrylate (7 ml) and the resulting solution was heated at 80° (bath temperature) for 1.5 hours. The bulk of the benzyl acrylate was then removed by distillation at 100° (bath temperature)/0.5 mm Hg pressure; and the resulting residue was chromatography on silica gel (25 g) using 1:9→1:4 ethyl acetate/petroleum ether (b,p. 60°-80°) to give, in order of elution, the following compounds: (5R)-11-benzyloxycarbonyl-3-oxo-6-oxa-2-azatricyclo[5.4.0.02,5 ]-undec-7,8-ene as colourless prisms (20 mg), isomer I of the title compound as a colourless gum (80 mg), and isomer II of the title compounds as a colourless gum (55 mg).

Aufarbeitung

  1. temperaturethe resulting solution was heated at 80° (bath temperature) for 1.5 hours
  2. customThe bulk of the benzyl acrylate was then removed by distillation at 100° (bath temperature)/0.5 mm Hg pressure
  3. custom1:9→1:4 ethyl acetate/petroleum ether (b,p. 60°-80°)
  4. customto give, in order of elution

Quellen und Nachweise

ORD-Eintrag
ord-e07042371b3b4d98af1cd6e8f1242e11
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04415584

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