Trifluoromethanesulfonic acid → CID 140386399

HRID 362103Notes

Reaction equation

HRID 362103 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]([C:35](=[NH:50])[NH:36][C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=4)=[O:38])[CH2:31][CH2:30]3)=[O:28])[CH2:10]2)=CC=1.[F:53][C:54]([F:60])([F:59])[S:55]([OH:58])(=[O:57])=[O:56]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[F:53][C:54]([F:60])([F:59])[S:55]([OH:58])(=[O:57])=[O:56].[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[CH2:34][CH2:33][N:32]([C:35](=[NH:50])[NH:36][C:37]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([N+:47]([O-:49])=[O:48])=[CH:45][CH:46]=3)=[O:38])[CH2:31][CH2:30]2)=[O:28])[CH2:10]1

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 141564120(4-nitrophenyl)methyl (2S,4S)-4-[(4-methoxyphenyl)methylsulfanyl]-2-[4-[N-[(4-nitrophenyl)methoxycarbonyl]carbamimidoyl]piperazine-1-carbonyl]pyrrolidine-1-carboxylate

Product 1

HCID 140386399CID 140386399

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

880 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(4-nitrobenzyloxycarbonylamidino)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (d) above] were dissolved in a mixture of 4.4 ml of trifluoroacetic acid and 0.88 ml of anisole, and then 160 μl of trifluoromethanesulfonic acid were added dropwise to this solution, whilst stirring and ice-cooling. The resulting mixture was then stirred at room temperature for 3 hours, after which it was concentrated by evaporation under reduced pressure. The resulting residue was washed three times with diethyl ether, and the powder thus formed was dried to obtain 918 mg of the title compound, as a powder.

Workup

  1. temperatureice-cooling
  2. stirringThe resulting mixture was then stirred at room temperature for 3 hours
  3. concentrationafter which it was concentrated by evaporation under reduced pressure
  4. washThe resulting residue was washed three times with diethyl ether
  5. customthe powder thus formed
  6. customwas dried

Sources & evidence

ORD record
ord-70b50ad180554cc395a27da1f5cd194c
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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