반응 #82989

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3-Benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

p-toluenesulfonic acid monohydrate

sodium carbonate

→

ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

용매

ethanol

반응 조건

후처리

1. 1
   온도heating the mixture
2. 2
   온도under reflux for 8 hours
3. 3
   농축concentrating the mixture under reduced pressure
4. 4
   workup.ADDITIONadding a saturated aqueous sodium bicarbonate to the reaction residue
5. 5
   추출extracting it with ethyl acetate
6. 6
   세척washing the extraction solution successively with water and saturated aqueous NaCl solution
7. 7
   건조drying it over anhydrous magnesium sulfate
8. 8
   농축concentrating the resulting solution

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.

출처