Réaction #5174

Équation de réaction

sodium hydroxide

4-methoxybenzyl mercaptan

(2S, 4R)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-methanesulfonyloxypyrrolidine

→

title compound

Rendement 31.3%

(2S, 4S)-1-(t-Butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine

Rendement 31.3%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was then stirred at room temperature for 30 minutes
2. 2
   workup.WAITat 40° C. for 6 hours
3. 3
   workup.ADDITIONAt the end of this time, it was treated
4. 4
   Autrepurified
5. 5
   Autredescribed in Preparation 1-(4)

Mode opératoire

151 mg of sodium hydroxide (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 532 mg of 4-methoxybenzyl mercaptan dissolved in 10 ml of dry dimethylformamide. The mixture was then stirred at room temperature for 30 minutes, after which 1.05 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-methanesulfonyloxypyrrolidine [prepared as described in step (2) above] was added. The reaction mixture was then stirred at room temperature for 30 minutes and then at 40° C. for 6 hours. At the end of this time, it was treated and purified according to the procedure described in Preparation 1-(4), to afford 385 mg of the title compound as an oil.

Source