Sodium Chloride → (2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-methanesulfonyloxypyrrolidine

HRID 5099Notes

Reaction equation

HRID 5099 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([OH:25])[CH2:22][C@H:21]1[C:26](=[O:30])[NH:27][CH2:28][CH3:29])=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[Na+]>O1CCCC1>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([O:25][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:22][C@H:21]1[C:26](=[O:30])[NH:27][CH2:28][CH3:29])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57061747(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine

Product 1

HCID 57182446(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-methanesulfonyloxypyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.81 ml of triethylamine and subsequently 7.65 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 23.20 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine dissolved in 250 ml of dry tetrahydrofuran, and then the mixture was stirred at 0° to 5° C. for 30 minutes. 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. The solvent was then removed by distillation under reduced pressure, to afford 26.54 g of the title compound as colorless crystals, melting at 138°-140° 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. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f4c935bb908045d3944dae4cba5fcbe4
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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