Sodium Carbonate → Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

HRID 54711노트

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HRID 54711 반응식
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH:11]2[C:15]([OH:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:20]1(C)C=CC(S(O)(=O)=O)=C[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([N:8]1[C:9](=[O:18])[CH:10]2[CH:12]([CH:11]2[C:15]([O:17][CH2:20][CH3:21])=[O:16])[C:13]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 199597233-Benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

생성물 1

HCID 15713436Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate수율 726.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

3-Benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (1.50 g, 6.13 mmol) was suspended in ethanol (30 ml), followed by adding p-toluenesulfonic acid monohydrate (145 mg, 0.76 mmol), heating the mixture under reflux for 8 hours, adding sodium carbonate to the reaction solution for neutralization, concentrating the mixture under reduced pressure, adding a saturated aqueous sodium bicarbonate to the reaction residue, extracting it with ethyl acetate, washing the extraction solution successively with water and saturated aqueous NaCl solution, drying it over anhydrous magnesium sulfate, concentrating the resulting solution to obtain ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate (1.51 g, 5.52 mmol, 90%), and recrystallizing it from ethanol to obtain a pure product.

후처리

  1. temperatureheating the mixture
  2. temperatureunder reflux for 8 hours
  3. concentrationconcentrating the mixture under reduced pressure
  4. additionadding a saturated aqueous sodium bicarbonate to the reaction residue
  5. extractionextracting it with ethyl acetate
  6. washwashing the extraction solution successively with water and saturated aqueous NaCl solution
  7. dry with materialdrying it over anhydrous magnesium sulfate
  8. concentrationconcentrating the resulting solution

출처 및 근거

ORD 기록
ord-cfda687b248c4bf8a753c8ad23c1ad55
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623078

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