Trifluoroacetic acid → HCID 11017253, compound

HRID 727638Notes

Reaction equation

HRID 727638 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.COC1C=CC(C[S:23][C@@H:24]2[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C@H:26]([C:42]([N:44]3[CH2:48][CH2:47][C@H:46]([NH:49][C:50]([O:52][CH2:53][C:54]4[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][CH:55]=4)=[O:51])[CH2:45]3)=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1.C(OCC)(=O)C>[SH:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([C:42]([N:44]2[CH2:48][CH2:47][C@H:46]([NH:49][C:50]([O:52][CH2:53][C:54]3[CH:55]=[CH:56][C:57]([N+:60]([O-:62])=[O:61])=[CH:58][CH:59]=3)=[O:51])[CH2:45]2)=[O:43])[CH2:25]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 11136222HCID 11136222, compound

Product 1

HCID 11017253HCID 11017253, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

12 ml of trifluoroacetic acid and 0.38 ml of trifluoromethanesulfonic acid were added to a suspension of 1.47 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in 2.3 ml of anisole, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed with hexane to remove the anisole, and then diethyl ether was added. The mixture was then cooled to -78° C., and the solidified product was broken up and separated by decantation. Several repetitions of this procedure yielded a powder and oily materials, which were dissolved in 100 ml of ethyl acetate to give a solution. The resulting solution was washed with an aqueous solution of sodium hydrogencarbonate, and the aqueous washings were extracted with 30 ml of ethyl acetate. The washings were combined with the ethyl acetate solution, and the combined organic phase was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.26 g 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 residue was washed with hexane
  3. customto remove the anisole
  4. additiondiethyl ether was added
  5. temperatureThe mixture was then cooled to -78° C.
  6. customseparated by decantation
  7. customSeveral repetitions of this procedure yielded a powder and oily materials, which
  8. customto give a solution
  9. washThe resulting solution was washed with an aqueous solution of sodium hydrogencarbonate
  10. extractionthe aqueous washings were extracted with 30 ml of ethyl acetate
  11. washthe combined organic phase was washed with an aqueous solution of sodium chloride
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-05387028e2e04842b4a48020ce49b475
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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