Réaction #5164

Équation de réaction

sodium bicarbonate

dioxane

hydrogen chloride

(2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine

→

title compound

Rendement 97.5%

(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

Rendement 97.5%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   Extractionwas extracted with ethyl acetate
3. 3
   LavageThe extract was washed with an aqueous solution of sodium chloride
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   AutreThe solvent was then removed by distillation under reduced pressure

Mode opératoire

1.92 g of (2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] was dissolved in 25 ml of ethyl acetate, and 26.2 ml of a 4N dioxane solution of hydrogen chloride were added to the solution, whilst ice-cooling. The mixture was then stirred at 0° to 5° C. for 2 hours and at room temperature for 30 minutes. At the end of this time, it was poured into a saturated aqueous solution of sodium bicarbonate, to make it weakly basic, and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.36 g of the title compound as a powder, melting at 120°-121° C.

Source