Hydrochloric Acid → (2S,4S)-4-(4-Methoxybenzylthio)-2-(1-piperazinyl-carbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride

HRID 362018Notes

Reaction equation

HRID 362018 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:44]=[CH:43][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][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]3)=[O:29])[CH2:11]2)=[CH:6][CH:5]=1>C(OCC)(=O)C>[ClH:1].[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][NH:33][CH2:32][CH2:31]3)=[O:29])[CH2:11]2)=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57015053(2S,4S)-4-(4-Methoxybenzylthio)-2-(4-t-butoxycarbonylpiperazin-1-ylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 67585358(2S,4S)-4-(4-Methoxybenzylthio)-2-(1-piperazinyl-carbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

27 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 5.2 g of (2S,4S)-4-(4-methoxybenzylthio)-2-(4-t-butoxycarbonylpiperazin-1-ylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (i) above] in 27 ml of ethyl acetate, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the reaction mixture was concentrated to dryness by evaporation under reduced pressure, and the resulting concentrate was triturated with diethyl ether. The powder thus obtained was collected by filtration and dried to give 4.2 g of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated to dryness by evaporation under reduced pressure
  4. concentrationthe resulting concentrate
  5. customwas triturated with diethyl ether
  6. customThe powder thus obtained
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-7f96a65f05f244719696b21bdcea9fef
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

Loading…