Trifluoroacetic acid → HCID 86753698, compound

HRID 362076Notes

Reaction equation

HRID 362076 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].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[CH2:49][CH2:48][N:47]([CH2:50][C:51]([O:53][CH2:54][C:55]4[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=4)=[O:52])[CH2:46][CH2:45]3)=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[F:8][C:9]([F:15])([F:14])[S:10]([OH:13])(=[O:12])=[O:11].[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[CH2:45][CH2:46][N:47]([CH2:50][C:51]([O:53][CH2:54][C:55]3[CH:56]=[CH:57][C:58]([N+:61]([O-:63])=[O:62])=[CH:59][CH:60]=3)=[O:52])[CH2:48][CH2:49]2)=[O:43])[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 57125058HCID 57125058, compound

Product 1

HCID 86753698HCID 86753698, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

8.0 ml of trifluoroacetic acid and 160 μl of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a suspension of 1120 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-piperazinecarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine in 1.75 ml of anisole, and the resulting mixture was stirred at room temperature for 1.5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was repeatedly washed with diethyl ether by decantation and dried in vacuo, to afford 1.58 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 resulting residue was repeatedly washed with diethyl ether by decantation
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e5f33975936641adb8eefbfd0814e10c
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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