(2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-methylpiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride → (2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-4-(N-4-nitrobenzyloxycarbonylacetimidoyl)-3-methylpiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727625
Cl.[CH3:2][O:3][C:4]1[CH:38]=[CH:37][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:35][CH2:34][NH:33][C@@H:32]([CH3:36])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:6][CH:5]=1.[N+:39]([C:42]1[CH:55]=[CH:54][C:45]([CH2:46][O:47][C:48]([NH:50][C:51](=N)[CH3:52])=[O:49])=[CH:44][CH:43]=1)([O-:41])=[O:40]>C(#N)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:51](=[N:50][C:48]([O:47][CH2:46][C:45]4[CH:54]=[CH:55][C:42]([N+:39]([O-:41])=[O:40])=[CH:43][CH:44]=4)=[O:49])[CH3:52])[C@@H:32]([CH3:36])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:37][CH:38]=1

Komponenten

4

Edukt 2

HCID 67585387(2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-methylpiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochlorideHCID 140352007HCID 140352007, Verbindung

Produkt 1

HCID 88299347(2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-4-(N-4-nitrobenzyloxycarbonylacetimidoyl)-3-methylpiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.26 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-methylpiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in step (i) above] were mixed with 1.14 g of N-(4-nitrobenzyloxycarbonyl)acetamidine and 45 ml of acetonitrile, and the mixture was heated under reflux for 16 hours. At the end of this time, the reaction mixture was worked up and purified by the same procedure as described in Preparation 1(ii), to give 922 mg of the title compound, as a powder.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. custompurified by the same procedure
  4. customas described in Preparation 1(ii)

Quellen und Nachweise

ORD-Eintrag
ord-eaf7e7548b7b4b85a6ebd8f2bef5f431
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712267

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