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

HRID 727623Notes

Reaction equation

HRID 727623 reaction equation
C(Cl)Cl.Cl.[CH3:5][O:6][C:7]1[CH:41]=[CH:40][C:10]([CH2:11][S:12][C@@H:13]2[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])[C@H:15]([C:31]([N:33]3[CH2:39][CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[O:32])[CH2:14]2)=[CH:9][CH:8]=1.[N+:42]([C:45]1[CH:58]=[CH:57][C:48]([CH2:49][O:50][C:51]([NH:53][C:54](=N)[CH3:55])=[O:52])=[CH:47][CH:46]=1)([O-:44])=[O:43]>CO>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][S:12][C@@H:13]2[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=3)=[O:19])[C@H:15]([C:31]([N:33]3[CH2:39][CH2:38][CH2:37][N:36]([C:54](=[N:53][C:51]([O:50][CH2:49][C:48]4[CH:57]=[CH:58][C:45]([N+:42]([O-:44])=[O:43])=[CH:46][CH:47]=4)=[O:52])[CH3:55])[CH2:35][CH2:34]3)=[O:32])[CH2:14]2)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22881639(2S,4S)-4-(4-methoxybenzylthio)-2-(1-homopiperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochlorideHCID 140352007HCID 140352007, compound

Product 1

HCID 88299641(2S,4S)-4-(4-Methoxybenzylthio)-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)homopiperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 14.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25 ml of methylene chloride were added to a solution of 2.5 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(1-homopiperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in step (i) above] in 25 ml of methanol, which was being heated under reflux, and then 904 mg of N-(4-nitrobenzyloxycarbonyl)acetamidine were added to the resulting mixture. The reaction mixture was heated under reflux for a further 5 hours, after which it was worked up and purified by the same procedure as described in Preparation 1(iii), to give 415 mg of the title compound, as a powder.

Workup

  1. temperaturewas being heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for a further 5 hours
  5. custompurified by the same procedure
  6. customas described in Preparation 1(iii)

Sources & evidence

ORD record
ord-4db9d744e1dd44aebdcad637f5d6aa0c
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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