(2S,4S)-4-(4-Methoxybenzylthio)-2-(1-piperazinyl-carbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride → (2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylformimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727626
Cl.[CH3:2][O:3][C:4]1[CH:37]=[CH:36][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][CH2:32][CH2:31]3)=[O:29])[CH2:11]2)=[CH:6][CH:5]=1.[N+:38]([C:41]1[CH:53]=[CH:52][C:44]([CH2:45][O:46][C:47]([NH:49][CH:50]=N)=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39]>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]([CH:50]=[N:49][C:47]([O:46][CH2:45][C:44]4[CH:52]=[CH:53][C:41]([N+:38]([O-:40])=[O:39])=[CH:42][CH:43]=4)=[O:48])[CH2:32][CH2:31]3)=[O:29])[CH2:11]2)=[CH:36][CH:37]=1

Komponenten

4

Edukt 2

HCID 67585358(2S,4S)-4-(4-Methoxybenzylthio)-2-(1-piperazinyl-carbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochlorideHCID 140386401(4-nitrophenyl)methyl N-methanimidoylcarbamate

Produkt 1

HCID 88299047(2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylformimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 5.51 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in Preparation 1(ii)] and 2.45 g of N-(4-nitrobenzyloxycarbonyl)formamidine in 10 ml of dry acetonitrile was stirred for 2 hours on a water-bath kept at 50° C. At the end of this time, the reaction mixture was freed from impurities by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 6:4 by volume mixture of ethyl acetate and acetonitrile as the eluent, to give 5.48 g of the title compound, as a powder.

Aufarbeitung

  1. customkept at 50° C
  2. filtrationAt the end of this time, the reaction mixture was freed from impurities by filtration
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and acetonitrile as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-817fe4f249d74ec88e2ff54d554d5ca6
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712267

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