Trifluoroacetic acid → 3-Mercapto-2-pyrrolidinone trifluoromethanesulfonate

HRID 5118

Reaction equation

HRID 5118 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

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 102432413-(4-Methoxybenzylthio)pyrrolidin-2-one

Product 1

HCID 197972633-Mercapto-2-pyrrolidinone trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

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.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customto leave a residue, which
  3. customwas purified by column chromatography through silica gel
  4. washeluted with a 10:1 by volume mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-715795a169ab49eca88ae924fb7a34b7
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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