반응 #5163

반응 방정식

sodium chloride

methanesulfonyl chloride

(2S, 4R)-1-(t-butoxycarbonyl)-2-carbamoyl-4-hydroxypyrrolidine

triethylamine

→

title compound

(2S, 4R)-1-(t-Butoxycarbonyl)-2-carbamoyl-4-methanesulfonyloxypyrrolidine

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척The extract was washed with an aqueous solution of sodium chloride
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타the solvent was removed by distillation under reduced pressure
5. 5
   기타The residue was purified by chromatography through silica gel (
6. 6
   세척eluted with a 9:1 by volume mixture of ethyl acetate and methanol)

실험 절차

1.85 ml of methanesulfonyl chloride was added, whilst ice-cooling, to a solution of 5.0 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-carbamoyl-4-hydroxypyrrolidine [prepared as described in step (2) above] in 250 ml of dry tetrahydrofuran, followed by 3.31 ml of triethylamine. The mixture was then stirred at 0° to 5° C. for 1 hour, after which it was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography through silica gel (eluted with a 9:1 by volume mixture of ethyl acetate and methanol) to afford 5.5 g of the title compound as colorless crystals.

출처