Reaktion #65623

Reaktionsgleichung

triethylamine

methanesulfonyl chloride

(2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

tetrahydrofuran

→

title compound

(2S,4S)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.WAITat room temperature for 1 hour
3. 3
   EinengenThe reaction mixture was then concentrated by evaporation under reduced pressure
4. 4
   workup.ADDITIONthe residue was mixed with an aqueous solution of sodium hydrogencarbonate
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe extract was washed with an aqueous solution of sodium chloride
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Sonstigethe solvent was then removed by distillation under reduced pressure

Vorschrift

89 μl of triethylamine and 50 μl of methanesulfonyl chloride were added to a solution of 321 mg of (2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 3.2 ml of anhydrous tetrahydrofuran, whilst ice-cooling, and the resulting mixture was stirred at 0° to 5° C. for 30 minutes and then at room temperature for 1 hour. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was mixed with an aqueous solution of sodium hydrogencarbonate and then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure, to afford 345 mg of the title compound as a powder.

Quelle