Clavulanic Acid → HCID 22807221, compound

HRID 1649172Notes

Reaction equation

HRID 1649172 reaction equation
[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]

Participants

3

Reactant 1

HCID 5280980Clavulanic Acid

Product 1

HCID 22807221HCID 22807221, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 75617Benzyl acrylateSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-e07042371b3b4d98af1cd6e8f1242e11
Source dataset
uspto-grants-1983_11
Patent number
US04415584

Reaction notes

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