Clavulanic Acid → HCID 22807221、化合物

HRID 1649173ノート

反応式

HRID 1649173 の反応式
[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]

参加物

4

反応物 2

HCID 5280980Clavulanic AcidHCID 19067483HCID 19067483、化合物

生成物 1

HCID 22807221HCID 22807221、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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°)

出典と根拠

ORDレコード
ord-d3add0e5fe0f49b9b93997a9169325ff
出典データセット
uspto-grants-1983_11
特許番号
US04415584

反応ノート

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