Реакция #5197

Уравнение реакции

hydrogen chloride

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

sodium bicarbonate

→

title compound

Выход 82.5%

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

Выход 82.5%

Растворители

ethyl acetate

ethyl acetate

Условия реакции

Обработка

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

Методика

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.

Источник