Reacción #5163

Ecuación de reacción

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe extract was washed with an aqueous solution of sodium chloride
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Otrothe solvent was removed by distillation under reduced pressure
5. 5
   OtroThe residue was purified by chromatography through silica gel (
6. 6
   Lavadoeluted with a 9:1 by volume mixture of ethyl acetate and methanol)

Procedimiento

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.

Fuente