Reaktion #814820

Reaktionsgleichung

trifluoromethanesulfonic acid

trifluoroacetic acid

(2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

→

title compound

Ausbeute 103.7%

(2S,4S)-4-mercapto-2-[(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Ausbeute 103.7%

Lösungsmittel

anisole

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt the end of this time, the solvent was removed by distillation under reduced pressure
2. 2
   Waschenthe residue was washed with hexane
3. 3
   Sonstigeto remove the anisole
4. 4
   workup.ADDITIONdiethyl ether was added
5. 5
   TemperaturThe mixture was then cooled to -78° C.
6. 6
   Sonstigeseparated by decantation
7. 7
   SonstigeSeveral repetitions of this procedure yielded a powder and oily materials, which
8. 8
   Sonstigeto give a solution
9. 9
   WaschenThe resulting solution was washed with an aqueous solution of sodium hydrogencarbonate
10. 10
    Extraktionthe aqueous washings were extracted with 30 ml of ethyl acetate
11. 11
    Waschenthe combined organic phase was washed with an aqueous solution of sodium chloride
12. 12
    Trocknendried over anhydrous magnesium sulfate
13. 13
    SonstigeThe solvent was then removed by distillation under reduced pressure

Vorschrift

12 ml of trifluoroacetic acid and 0.38 ml of trifluoromethanesulfonic acid were added to a suspension of 1.47 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in 2.3 ml of anisole, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed with hexane to remove the anisole, and then diethyl ether was added. The mixture was then cooled to -78° C., and the solidified product was broken up and separated by decantation. Several repetitions of this procedure yielded a powder and oily materials, which were dissolved in 100 ml of ethyl acetate to give a solution. The resulting solution was washed with an aqueous solution of sodium hydrogencarbonate, and the aqueous washings were extracted with 30 ml of ethyl acetate. The washings were combined with the ethyl acetate solution, and the combined organic phase 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 give 1.26 g of the title compound, as a powder.

Quelle