Trifluoroacetic acid → HCID 86747835, compound

HRID 1033667Notes

Reaction equation

HRID 1033667 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]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.[F:45][C:46]([F:52])([F:51])[S:47]([OH:50])(=[O:49])=[O:48]>C1(OC)C=CC=CC=1>[F:45][C:46]([F:52])([F:51])[S:47]([OH:50])(=[O:49])=[O:48].[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]([N:29]2[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]2)=[O:28])[CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 15282185HCID 15282185, compound

Product 1

HCID 86747835HCID 86747835, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

305 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-(4-methyl-1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 1) were suspended in 627 μl of anisole, and then the suspension was placed over an ice bath. 3.14 ml of trifluoroacetic acid and 56 μl of trifluoromethanesulfonic acid were then added to the suspension, 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 residue was washed with diethyl ether by repeated decantation, after which it was dried under reduced pressure to obtain 318 mg of the title compound.

Workup

  1. customthe suspension was placed over an ice bath
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. washThe residue was washed with diethyl ether by repeated decantation
  4. customafter which it was dried under reduced pressure

Sources & evidence

ORD record
ord-4053236910824a05b6823d7ef9b0cd64
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

Loading…