Réaction #82989

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températureheating the mixture
2. 2
   Températureunder reflux for 8 hours
3. 3
   Concentrationconcentrating the mixture under reduced pressure
4. 4
   workup.ADDITIONadding a saturated aqueous sodium bicarbonate to the reaction residue
5. 5
   Extractionextracting it with ethyl acetate
6. 6
   Lavagewashing the extraction solution successively with water and saturated aqueous NaCl solution
7. 7
   Séchagedrying it over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrating the resulting solution

Mode opératoire

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.

Source