Hydrochloric Acid → (2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1033682Notes

Reaction equation

HRID 1033682 reaction equation
Cl.C([S:5][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][O:34][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])[CH2:28][CH2:27]2)=[O:25])[CH2:7]1)(=O)C.C(OCC)(=O)C.CO>O1CCOCC1>[SH:5][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[C@H:8]([C:24]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][O:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)=[O:36])[CH2:30][CH2:31]2)=[O:25])[CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 57136373(2S,4S)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 15814079(2S,4S)-4-Mercapto-2-{4-[2-(p-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

600 ml of a methanolic solution containing 10% w/v hydrogen chloride were added to a solution of 140 g of (2S,4S)-4-acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl] -1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine dissolved in 150 ml of dioxane, and the resulting mixture was stirred at 50° C. for 1 hour. At the end of this time, the mixture was concentrated by evaporation under reduced pressure, and the concentrate was diluted with 1500 ml of ethyl acetate, after which it was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The mixture was then washed with 300 ml of water and with 300 ml of an aqueous solution of sodium chloride, after which it was freed from the solvent by distillation under reduced pressure. The residue thus obtained was subjected to column chromatography through silica gel using mixtures of ethyl acetate and methanol ranging from 30:1 to 20:1 by volume as the eluent. Those fractions containing the desired compound were collected and concentrated to afford 96.44 g of the title compound as a colorless powder.

Workup

  1. concentrationAt the end of this time, the mixture was concentrated by evaporation under reduced pressure
  2. additionthe concentrate was diluted with 1500 ml of ethyl acetate
  3. washThe mixture was then washed with 300 ml of water and with 300 ml of an aqueous solution of sodium chloride
  4. distillationafter which it was freed from the solvent by distillation under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-02c9d5204dc249b9b239e57c5e8118e1
Source dataset
uspto-grants-1994_05
Patent number
US05310735

Reaction notes

Loading…