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

HRID 1033675Notes

Reaction equation

HRID 1033675 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[C:16]([O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([C@@H:30]2[CH2:34][C@H:33]([S:35]CC3C=CC(OC)=CC=3)[CH2:32][N:31]2[C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[CH:51][CH:50]=2)=[O:46])=[O:29])[CH2:24][CH2:23]1)(=[O:18])[NH2:17]>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[C:16]([O:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:28]([C@@H:30]2[CH2:34][C@H:33]([SH:35])[CH2:32][N:31]2[C:45]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]([N+:55]([O-:57])=[O:56])=[CH:53][CH:54]=2)=[O:46])=[O:29])[CH2:26][CH2:27]1)(=[O:18])[NH2:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 57049434(2S,4S)-2-[4-(2-carbamoyloxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 86747840(2S,4S)-2-[4-(2-Carbamoyloxyethyl)-1-piperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.67 ml of trifluoroacetic acid and 122 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 417 mg of (2S,4S)-2-[4-(2-carbamoyloxyethyl)-1-piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 9) in 753 μl of anisole, and the resulting mixture was stirred at the same 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 repeated decantation and dried under reduced pressure to give 325 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 repeated decantation
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-d56c04a7d9234d91a02242aeb8a85d12
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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