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

HRID 362019Notes

Reaction equation

HRID 362019 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 4hours. 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.

Workup

  1. temperaturewhilst heating the solution
  2. temperatureunder reflux
  3. temperatureThe resulting mixture was then heated
  4. temperatureunder reflux for a further 4hours
  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

Sources & evidence

ORD record
ord-c8f26c7519554af6a0a37f04236f6573
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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