Sodium Chloride → (2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 5104Notes

Reaction equation

HRID 5104 reaction equation
[CH2:1](I)[CH3:2].C(=O)(O)[O-].[Na+].[CH3:9][O:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][S:16][C@@H:17]2[CH2:21][NH:20][C@H:19]([C:22](=[O:25])[NH:23][CH3:24])[CH2:18]2)=[CH:13][CH:12]=1.[Cl-].[Na+]>CN(C)C=O>[CH2:1]([N:20]1[CH2:21][C@@H:17]([S:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:27][CH:26]=2)[CH2:18][C@H:19]1[C:22](=[O:25])[NH:23][CH3:24])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 14880277(2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Product 1

HCID 57039848(2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.71 ml of ethyl iodide and 742 mg of sodium bicarbonate were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 20 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 1 hour and then at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluted with ethyl acetate), to afford 1.87 g of the title compound as colorless crystals, melting at 68°-70° C.

Workup

  1. waitat room temperature for 5 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. customafter which the solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-bf4b72bd1c12477f9a2610f9db0493f3
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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