Reaktion #449294

Reaktionsgleichung

1,2-dichloroethane

trifluoroacetic acid

trifluoromethanesulfonic acid

(2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidine

→

title compound

Ausbeute 75.1%

(2S, 4S)-4-Mercapto-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidine

Ausbeute 75.1%

Lösungsmittel

anisole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling, to the resulting solution
2. 2
   Sonstigethe solvent was removed by evaporation under reduced pressure
3. 3
   WaschenThe resulting residue was washed
4. 4
   workup.ADDITIONThe residue was diluted with ethyl acetate
5. 5
   workup.ADDITIONby the addition of an aqueous solution of sodium hydrogencarbonate
6. 6
   WaschenThe ethyl acetate layer was washed with water and with an aqueous solution of sodium chloride, in that order
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated by evaporation under reduced pressure

Vorschrift

0.73 g of (2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidine [prepared as described in step (b) above] was dissolved in 1.53 ml of anisole, and 7.25 ml of trifluoroacetic acid and 0.25 ml of trifluoromethanesulfonic acid were added dropwise, whilst ice-cooling, to the resulting solution. The mixture was then stirred at room temperature for 90 minutes, after which 1,2-dichloroethane was added to the reaction mixture and the solvent was removed by evaporation under reduced pressure. The resulting residue was washed by repeated decantation, in turn, with hexane and with diethyl ether. The residue was diluted with ethyl acetate and was made alkaline by the addition of an aqueous solution of sodium hydrogencarbonate. The ethyl acetate layer was washed with water and with an aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 420 mg of the title compound, in the form of an amorphous powder.

Quelle