Trifluoroacetic acid → 3-Mercapto-2-pyrrolidinone trifluoromethanesulfonate
Reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].COC1C=CC(C[S:23][CH:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])=CC=1>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[SH:23][CH:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29]Participants
5
Procedure
20 ml of trifluoroacetic acid and 0.41 ml of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 949 mg of 3-(4-methoxybenzylthio)pyrrolidin-2-one in 4 ml of anisole, and then the mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to leave a residue, which was purified by column chromatography through silica gel, eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 728 mg of the title compound as an oil.