反応 #5163

反応方程式

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

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典