Réaction #5197

Équation de réaction

hydrogen chloride

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

sodium bicarbonate

→

title compound

Rendement 82.5%

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

Rendement 82.5%

Solvants

ethyl acetate

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   Extractionextracted with tetrahydrofuran
3. 3
   LavageThe combined extracts were washed with an aqueous solution of sodium chloride
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Autrethe solvent was removed by distillation under reduced pressure
6. 6
   Lavageeluted with a 87:13 by volume mixture of ethyl acetate and methanol)

Mode opératoire

41.19 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 13.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The aqueous layer was saturated with ammonium chloride and extracted with tetrahydrofuran. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (eluted with a 87:13 by volume mixture of ethyl acetate and methanol) to afford 8.00 g of the title compound as pale brown crystals, melting at 67°-68° C.

Source