反应 #5163

反应方程式

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

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   萃取extracted with ethyl acetate
2. 2
   洗涤The extract was washed with an aqueous solution of sodium chloride
3. 3
   干燥dried over anhydrous magnesium sulfate
4. 4
   其他the solvent was removed by distillation under reduced pressure
5. 5
   其他The residue was purified by chromatography through silica gel (
6. 6
   洗涤eluted with a 9:1 by volume mixture of ethyl acetate and methanol)

实验过程

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.

来源