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 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.

1. temperaturecooling
2. waitat room temperature for 1 hour
3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
4. additionthe residue was mixed with an aqueous solution of sodium hydrogencarbonate
5. extractionextracted with ethyl acetate
6. washThe extract was washed with an aqueous solution of sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was then removed by distillation under reduced pressure

ORD record

ord-9c3e5abeeb5d409990059010882c1e9b

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05310735