Sodium Chloride → (2S, 4R)-1-(t-Butoxycarbonyl)-4-methanesulfonyloxy-2-methylcarbamoylpyrrolidine

HRID 5072Notes

Reaction equation

HRID 5072 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:16]1[C:21](=[O:24])[NH:22][CH3:23])=[O:14])([CH3:11])([CH3:10])[CH3:9].[CH3:25][S:26](Cl)(=[O:28])=[O:27].[Cl-].[Na+]>O1CCCC1>[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([O:20][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:17][C@H:16]1[C:21](=[O:24])[NH:22][CH3:23])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10847882tert-butyl (2S,4R)-4-hydroxy-2-(methylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 57179932(2S, 4R)-1-(t-Butoxycarbonyl)-4-methanesulfonyloxy-2-methylcarbamoylpyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.11 ml of triethylamine were added, whilst ice-cooling, to a solution of 11.29 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-methylcarbamoyl-4-hydroxypyrrolidine [prepared as described in step (1) above] dissolved in 120 ml of dry tetrahydrofuran, and then 3.93 ml of methanesulfonyl chloride were added to the resulting mixture, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 15° C. for 30 minutes. It 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. The solvent was then removed by distillation under reduced pressure, giving 11.58 g of the title compound as colorless crystals.

Workup

  1. waitat 15° C. for 30 minutes
  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 then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-2785b6e61574455283939136e0ff5801
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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