Sodium Chloride → (2S,4S)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37346Notes

Reaction equation

HRID 37346 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].[H-].[Na+].CS(O[C@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C@H:14]([C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][O:40][C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=3)=[O:42])[CH2:34][CH2:33]2)=[O:31])[CH2:13]1)(=O)=O.[Cl-].[Na+]>CN(C)C=O>[C:1]([S:3][C@@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C@H:14]([C:30]([N:32]2[CH2:33][CH2:34][N:35]([CH2:38][CH2:39][O:40][C:41]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][C:48]([N+:51]([O-:53])=[O:52])=[CH:49][CH:50]=3)=[O:42])[CH2:36][CH2:37]2)=[O:31])[CH2:13]1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 56974223(2S,4R)-4-Methanesulfonyloxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 178418634HCID 178418634, compound

Product 1

HCID 57136373(2S,4S)-4-Acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

51 μl of thioacetic acid were added to a suspension of 26 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) in 1.4 ml of anhydrous dimethylformamide, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 340 mg of (2S,4R)-4-methanesulfonyloxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (b1) above] in 2 ml of anhydrous dimethylformamide was added to the mixture, and the resulting mixture was stirred at 80°-90° C. for 4 hours, after which the reaction mixture was allowed to cool to room temperature. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified in a similar manner to that described in step (a), above, to afford the title compound (166 mg). The infra-red absorption spectrum and nuclear magnetic resonance spectrum of the product thus obtained were identical with those of the compound obtained as described in step (a), above.

Workup

  1. temperaturewhilst ice-cooling
  2. stirringthe resulting mixture was stirred at 80°-90° C. for 4 hours
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationfreed from the solvent by distillation under reduced pressure
  8. customThe residue was purified in a similar manner to that

Sources & evidence

ORD record
ord-fd42de73b6ea47fc93e7b29197eab70d
Source dataset
uspto-grants-1995_05
Patent number
US05420119

Reaction notes

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