Reaktion #449295

Reaktionsgleichung

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

trifluoroacetic acid

trifluoromethanesulfonic acid

→

title compound

Ausbeute 93.7%

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

Ausbeute 93.7%

Lösungsmittel

anisole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.WAITat room temperature for a further 1 hour
3. 3
   SonstigeAt the end of this time, the solvent was removed by distillation under reduced pressure
4. 4
   Waschenthe resulting residue was washed with hexane and with diethyl ether
5. 5
   Sonstigedried by evaporation under reduced pressure
6. 6
   workup.ADDITIONEthyl acetate was added to the whole of this compound
7. 7
   SonstigeThe ethyl acetate layer was separated
8. 8
   Waschenwashed with an aqueous solution of sodium chloride
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was removed by evaporation under reduced pressure

Vorschrift

610 mg of (2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(N-4-nitrobenzyloxycarbonylacetimidoylamino)azetidin-1-ylcarbonyl]pyrrolidine [prepared as described in step (a) above] were dissolved in 1.19 ml of anisole, and 4.23 ml of trifluoroacetic acid and 193 μl of trifluoromethanesulfonic acid were added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 1 hour under the same conditions and then at room temperature for a further 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was washed with hexane and with diethyl ether and dried by evaporation under reduced pressure, to convert it to the trifluoromethanesulfonate in the form of a powder. Ethyl acetate was added to the whole of this compound, followed by sufficient of a saturated aqueous solution of sodium hydrogencarbonate to make it alkaline. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure, to give 448 mg of the title compound as a powder.

Quelle