Trifluoroacetic acid → (2S,4S)-4-Mercapto-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl)-1-methylpyrrolidine bis(trifluoromethanesulfonate)

HRID 362065Notes

Reaction equation

HRID 362065 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[OH:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]([C@@H:27]2[CH2:31][C@H:30]([S:32]CC3C=CC(OC)=CC=3)[CH2:29][N:28]2[CH3:42])=[O:26])[CH2:21][CH2:20]1>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[SH:32][C@@H:30]1[CH2:29][N:28]([CH3:42])[C@H:27]([C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][OH:16])[CH2:24][CH2:23]2)=[O:26])[CH2:31]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 67612520HCID 67612520, compound

Product 1

HCID 86753695(2S,4S)-4-Mercapto-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl)-1-methylpyrrolidine bis(trifluoromethanesulfonate)

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

10 ml of trifluoroacetic acid and 520 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 1150 mg of (2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (i) above] in 3 ml of anisole, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, to give 1680 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

Sources & evidence

ORD record
ord-981708e218db43f6bd29d99133da710c
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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