Clavulanic Acid → HCID 22807221、化合物

HRID 1649172ノート

反応式

HRID 1649172 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=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]

参加物

3

反応物 1

HCID 5280980Clavulanic Acid

生成物 1

HCID 22807221HCID 22807221、化合物収率 83.3%

試薬・触媒・溶媒 1

HCID 75617Benzyl acrylate溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-e07042371b3b4d98af1cd6e8f1242e11
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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