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

HRID 362063Notes

Reaction equation

HRID 362063 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][C@@H:24]2[CH2:28][N:27]([CH3:29])[C@H:26]([C:30]([N:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)=[O:31])[CH2:25]2)=CC=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:23][C@@H:24]1[CH2:28][N:27]([CH3:29])[C@H:26]([C:30]([N:32]2[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]2)=[O:31])[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 57068274HCID 57068274, compound

Product 1

HCID 86752002(2S,4S)-4-Mercapto-2-(4-methyl-1-piperazinylcarbonyl)-1-methylpyrrolidine bis(trifluoromethanesulfonate)

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

10 ml of trifluoroacetic acid, followed by 510 liters of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 1050 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-(4-methyl-1-piperazinylcarbonyl)-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, and the residue was triturated with diethyl ether to cause solidification. The solid was washed with diethyl ether five times and dried, to give 1350 mg of the title compound as a powder.

Workup

  1. additionwere added, whilst ice-
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. customthe residue was triturated with diethyl ether
  4. washThe solid was washed with diethyl ether five times
  5. customdried

Sources & evidence

ORD record
ord-361c984a88de4635915ed750af1e51f6
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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