Clavulanic Acid → HCID 22807221, compound

HRID 1649173Notes

Reaction equation

HRID 1649173 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([N+]([O-])=O)=CC=1)(=O)C=C>C(OCC)(=O)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

4

Reactant 2

HCID 5280980Clavulanic AcidHCID 19067483HCID 19067483, compound

Product 1

HCID 22807221HCID 22807221, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

prepared from 1.01 g clavulanic acid according to Example 1) was dissolved in dry 1,2-dimeth xyethane (10 ml) containing hydroquinolinone (50 mg). p-Nitrobenzyl acrylate (1.8 g) was added to the solution which was then heated at 85° (bath temperature) with exclusion of moisture for 2.5 hours. The mixture was cooled, diluted with ethyl acetate (50 ml), and filtered. The solvent was evaporated from the filtrate under reduced pressure to give a yellow oil which was chromatographed on silica gel (15 g) using gradient elution from 1:7 to 1:3 ethyl acetate/petroleum ether (b.p. 60°-80°). In this way the title compound (Mixture of isomers) was obtained as a yellow gum (150 mg).

Workup

  1. dissolutionwas dissolved in dry 1,2-dimeth xyethane (10 ml)
  2. additioncontaining hydroquinolinone (50 mg)
  3. temperaturewas then heated at 85° (bath temperature) with exclusion of moisture for 2.5 hours
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customThe solvent was evaporated from the filtrate under reduced pressure
  7. customto give a yellow oil which
  8. customwas chromatographed on silica gel (15 g)
  9. washelution from 1:7 to 1:3 ethyl acetate/petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-d3add0e5fe0f49b9b93997a9169325ff
Source dataset
uspto-grants-1983_11
Patent number
US04415584

Reaction notes

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