Trifluoroacetic acid → HCID 86751997, compound

HRID 727642Notes

Reaction equation

HRID 727642 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]([NH:44][C@H:45]3[CH2:49][CH2:48][N:47]([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])[CH2:46]3)=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1>[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]([NH:44][C@H:45]2[CH2:49][CH2:48][N:47]([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])[CH2:46]2)=[O:43])[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 86751996HCID 86751996, compound

Product 1

HCID 86751997HCID 86751997, compoundYield 136.2%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

6.5 ml of trifluoroacetic acid and 0.21 ml of trifluoromethanesulfonic acid were added to a suspension of 835 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-3-ylaminocarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (iii) above] in 1.3 ml of anisole, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was first washed with hexane to remove the anisole and then mixed with diethyl ether. The mixture was cooled to -78° C., and the solidified product was broken up and separated by decantation. Several repetitions of this procedure yielded 940 mg of the title compound as a powder.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. washthe resulting residue was first washed with hexane
  4. customto remove the anisole
  5. additionmixed with diethyl ether
  6. temperatureThe mixture was cooled to -78° C.
  7. customseparated by decantation

Sources & evidence

ORD record
ord-492c06c503f74a6e995a9fe22654819b
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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