Sodium Chloride → HCID 57226141, compound

HRID 1030130Notes

Reaction equation

HRID 1030130 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][C@H:23](OS(C)(=O)=O)[CH2:22][C@H:21]1[C:30](=[O:32])[NH2:31])=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[Na+]>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@H:23]([S:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH2:22][C@H:21]1[C:30](=[O:32])[NH2:31])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 14880263(2S, 4R)-1-(t-Butoxycarbonyl)-2-carbamoyl-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57226141HCID 57226141, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

330 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 1.18 g of p-methoxybenzyl mercaptan in 25 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 2.14 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-carbamoyl-4-methanesulfonyloxypyrrolidine [prepared as described in step (3) above] were added to the mixture, which was then stirred at room temperature for 3 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 and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography through silica gel (eluted with a 2:3 by volume mixture of cyclohexane and ethyl acetate) to afford 1.94 g of the title compound as an oil.

Workup

  1. stirringwas then stirred at room temperature for 3 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. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by chromatography through silica gel (
  7. washeluted with a 2:3 by volume mixture of cyclohexane and ethyl acetate)

Sources & evidence

ORD record
ord-362bcf16e00b42b2a8f9599455781164
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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