반응 #5197

반응 방정식

hydrogen chloride

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

sodium bicarbonate

→

title compound

수율 82.5%

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

수율 82.5%

용매

ethyl acetate

ethyl acetate

반응 조건

후처리

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

실험 절차

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.

출처