Trifluoroacetic acid → (2S, 4S)-4-mercapto-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate

HRID 727622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727622
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]([C:50](=[N:52][C:53]([O:55][CH2:56][C:57]4[CH:62]=[CH:61][C:60]([N+:63]([O-:65])=[O:64])=[CH:59][CH:58]=4)=[O:54])[CH3:51])[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].[SH:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])[C@H:26]([C:42]([N:44]2[CH2:45][CH2:46][N:47]([C:50](=[N:52][C:53]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][C:60]([N+:63]([O-:65])=[O:64])=[CH:59][CH:58]=3)=[O:54])[CH3:51])[CH2:48][CH2:49]2)=[O:43])[CH2:25]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 88299204(2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 88299227(2S, 4S)-4-mercapto-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Versuchsvorschrift

3.2 ml of trifluoroacetic acid and 103 μl of trifluoromethanesulfonic acid were added to a solution of 430 mg of (2S,4S)-4-(4-methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (iii) above] in 636 μl of anisole, and the resulting mixture was stirred for 1 hour, whilst ice-cooling. An the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the residue was repeatedly washed with diethyl ether by decantation, to give 450 mg of the title compound, as a powder.

Aufarbeitung

  1. temperaturecooling
  2. distillationAn the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  3. washthe residue was repeatedly washed with diethyl ether by decantation

Quellen und Nachweise

ORD-Eintrag
ord-3258e55a6dc34cbf88904409e97dfd88
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712267

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