Clavulanic Acid → HCID 22807221, 화합물

HRID 1649172노트

반응식

HRID 1649172 반응식
[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]

참가 물질

3

반응물 1

HCID 5280980Clavulanic Acid

생성물 1

HCID 22807221HCID 22807221, 화합물수율 83.3%

시약·촉매·용매 1

HCID 75617Benzyl acrylate용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-e07042371b3b4d98af1cd6e8f1242e11
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415584

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