Trifluoroacetic acid → (2S,4S)-2-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362074Notes

Reaction equation

HRID 362074 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.[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[C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=2)=[O:43])=[O:26])[CH2:21][CH2:20]1>C1(OC)C=CC=CC=1>[OH:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([C:25]([C@@H:27]2[CH2:31][C@H:30]([SH:32])[CH2:29][N:28]2[C:42]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][C:49]([N+:52]([O-:54])=[O:53])=[CH:50][CH:51]=2)=[O:43])=[O:26])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 15282196(2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 15282197(2S,4S)-2-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 168.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.8 ml of trifluoroacetic acid and 91 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 288 mg of (2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 580 μl of anisole, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was washed with diethyl ether by decantation and dried in vacuo, to give 380 mg of the title compound, as a powder.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. washthe resulting residue was washed with diethyl ether by decantation
  3. customdried in vacuo

Sources & evidence

ORD record
ord-27cff5443a1348ac893719ea32a66423
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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