Dichloromethane → (2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727621노트

반응식

HRID 727621 반응식
C(Cl)Cl.[N+:4]([C:7]1[CH:20]=[CH:19][C:10]([CH2:11][O:12][C:13]([NH:15][C:16](=[NH:18])[CH3:17])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5].Cl.[CH3:22][O:23][C:24]1[CH:57]=[CH:56][C:27]([CH2:28][S:29][C@@H:30]2[CH2:34][N:33]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)=[O:36])[C@H:32]([C:48]([N:50]3[CH2:55][CH2:54]N[CH2:52][CH2:51]3)=[O:49])[CH2:31]2)=[CH:26][CH:25]=1>CO>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][S:29][C@@H:30]2[CH2:34][N:33]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)=[O:36])[C@H:32]([C:48]([N:50]3[CH2:55][CH2:54][N:18]([C:16](=[N:15][C:13]([O:12][CH2:11][C:10]4[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:20][CH:19]=4)=[O:14])[CH3:17])[CH2:52][CH2:51]3)=[O:49])[CH2:31]2)=[CH:56][CH:57]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 67585358(2S,4S)-4-(4-Methoxybenzylthio)-2-(1-piperazinyl-carbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochlorideHCID 140352007HCID 140352007, 화합물

생성물 1

HCID 88299204(2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 33.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

11 ml of methylene chloride, followed by 452 mg of N-(4-nitrobenzyloxycarbonyl)acetamidine, were added to a solution of 1.1 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in step (ii) above] in 22 ml of methanol, whilst heating the solution under reflux. The resulting mixture was then heated under reflux for a further 4 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of ethyl acetate and methanol as the eluent to give 466 mg of the title compound, as a powder.

후처리

  1. temperaturewhilst heating the solution
  2. temperatureunder reflux
  3. temperatureThe resulting mixture was then heated
  4. temperatureunder reflux for a further 4 hours
  5. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and methanol as the eluent

출처 및 근거

ORD 기록
ord-3a6c83e973b944caa813edd2ab7a1068
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712267

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