(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 362020노트

반응식

HRID 362020 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 5.51 g of (2S,4S)-4-(4-methoxy-benzylthio)-2-(1-piperazinylcarbonyl)-1-(4-nitrobenzyl-oxycarbonyl)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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a5dae6b17df4a58a155872e3ae99c1c
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866564

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