Sodium Chloride → (2S, 4S)-2-Ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

HRID 5102

Reaction equation

HRID 5102 reaction equation
[CH2:1](I)[CH3:2].C(=O)(O)[O-].[Na+].[CH2:9]([NH:11][C:12]([C@@H:14]1[CH2:18][C@H:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:16][NH:15]1)=[O:13])[CH3:10].[Cl-].[Na+]>CN(C)C=O>[CH2:9]([NH:11][C:12]([C@@H:14]1[CH2:18][C@H:17]([S:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:16][N:15]1[CH2:1][CH3:2])=[O:13])[CH3:10]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 14880286(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 14880288(2S, 4S)-2-Ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

301 μl of ethyl iodide and 314 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 8 ml of dry dimethylformamide, and the mixture was stirred 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 subjected to column chromatography through silica gel (eluted with ethyl acetate) to afford 982 mg of the title compound as colorless crystals, melting at 60°-61° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-07dfe390ff4e442aa0fab0ba3b5fab07
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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