Sodium Chloride → HCID 56999702, compound

HRID 5116Notes

Reaction equation

HRID 5116 reaction equation
[H-].[Na+].CS(O[CH2:8][CH2:9][N:10]1[CH2:14][C@@H:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[C:25](=[O:28])[NH:26][CH3:27])(=O)=O.[Cl-].[Na+]>CN(C)C=O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][S:15][C@@H:13]2[CH2:14][N:10]3[C@H:11]([C:25](=[O:28])[N:26]([CH3:27])[CH2:8][CH2:9]3)[CH2:12]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 57207810(2S, 4S)-1-(2-Methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Product 1

HCID 56999702HCID 56999702, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

347 mg of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 2.64 g of (2S, 4S)-1-(2-methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 30° C. for 2 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of acetonitrile and methanol), to afford 1.75 g of the title compound as an oil.

Workup

  1. waitat 30° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationfreed from the solvent by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel (
  7. washeluted with a 5:1 by volume mixture of acetonitrile and methanol),

Sources & evidence

ORD record
ord-f71993a5c79649908460f68d8e688e89
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

Loading…