Trifluoroacetic acid → HCID 86747839, compound

HRID 1033674Notes

Reaction equation

HRID 1033674 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([S:17]CC3C=CC(OC)=CC=3)[CH2:14][N:13]2[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[O:28])=[O:11])[CH2:6][CH2:5]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].[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([SH:17])[CH2:14][N:13]2[C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)=[O:28])=[O:11])[CH2:8][CH2:9]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 86747839HCID 86747839, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

288 mg of (2S,4S)-2-[4-(2-hydroxyethyl)piperazinylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 7) were dissolved in 560 μl of anisole, and the solution was placed on an ice bath. 2.8 ml of trifluoroacetic acid and 91 μl of trifluoromethanesulfonic acid were added to the solution, still on the ice bath, and the resulting mixture was stirred for 1 hour at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was washed with diethyl ether by repeated decantation, and then dried under reduced pressure, to give 380 mg of the title compound.

Workup

  1. customthe solution was placed on an ice bath
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. washThe resulting residue was washed with diethyl ether by repeated decantation
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bef64f65007845eba787f7af316f8d03
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

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