Trifluoroacetic acid → (2S, 4S)-4-Mercapto-2-(1-methyl-2-pyrrolidinylethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate)

HRID 1033668

Reaction equation

HRID 1033668 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27](=[O:37])[NH:28][CH:29]([CH3:36])[CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50]>C1(OC)C=CC=CC=1>[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50].[F:47][C:48]([F:54])([F:53])[S:49]([OH:52])(=[O:51])=[O:50].[SH:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([C:27](=[O:37])[NH:28][CH:29]([CH3:36])[CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 67781019(2S, 4S)-4-(4-methoxybenzylthio)-2-(1-methyl-2-pyrrolidinylethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 86747836(2S, 4S)-4-Mercapto-2-(1-methyl-2-pyrrolidinylethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate)

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

369 mg of (2S, 4S)-4-(4-methoxybenzylthio)-2-(1-methyl-2-pyrrolidinylethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 2) were suspended in 720 μl of anisole, and the suspension was placed on an ice bath. Maintaining the suspension on the ice bath, 3.6 ml of trifluoroacetic acid and 128 μl of trifluoromethanesulfonic acid were added to it, and it was then stirred for 1 hour at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure. The residue was washed with diethyl ether by repeated decantation and dried under reduced pressure, to give 440 mg of the title compound.

Workup

  1. customthe suspension was placed on an ice bath
  2. additionwere added to it, and it
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. washThe residue was washed with diethyl ether by repeated decantation
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9936235296c34f62be8d9c89d6719f17
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Linked notes

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