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

89 μl of triethylamine and 50 μl of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 321 mg of (2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinyl carbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 3.2 ml of dry tetrahydrofuran, and the resulting mixture was stirred at between 0° C. and 5° C. for 30 minutes and then at room temperature for a further 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate; the mixture was 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 removed by distillation under reduced pressure, to give 345 mg of the title compound as a powder.

1. waitat room temperature for a further 1 hour
2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
3. additionthe resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate
4. extractionthe mixture was then extracted with ethyl acetate
5. washThe extract was washed with an aqueous solution of sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was removed by distillation under reduced pressure

ORD record

ord-81da0c78ebc24fabbf5d6782c1c79e25

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05712267