Acetic Acid → 1-Benzenesulfonyl-2-oxo-3-acetoxy-5-ethoxy-pyrrolidine

HRID 476600Notes

Reaction equation

HRID 476600 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]([O:15][CH2:16][CH3:17])[CH2:13][CH:12]([OH:18])[C:11]2=[O:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](O)(=[O:22])[CH3:21]>>[C:1]1([S:7]([N:10]2[CH:14]([O:15][CH2:16][CH3:17])[CH2:13][CH:12]([O:18][C:20](=[O:22])[CH3:21])[C:11]2=[O:19])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 30781671-(Benzenesulfonyl)-5-ethoxy-3-hydroxypyrrolidin-2-one

Product 1

HCID 198380551-Benzenesulfonyl-2-oxo-3-acetoxy-5-ethoxy-pyrrolidine

Procedure

A solution of 0.50 g of 1-benzenesulfonyl-2-oxo-3-hydroxy-5-ethoxypyrrolidine (trans isomer) in 10 cm3 anhydrous acetic acid is heated to boiling for 1 hour. It is allowed to cool to room temperature and the acetic anhydride is evaporated. It is dissolved in toluene and the azeotrope is evaporated under reduced pressure. The residue is chromatographed on silica by elution with a mixture of ethylacetate-hexane (1-1); 0.48 g of the expected product is obtained.

Workup

  1. customthe acetic anhydride is evaporated
  2. dissolutionIt is dissolved in toluene
  3. customthe azeotrope is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica by elution with a mixture of ethylacetate-hexane (1-1)

Sources & evidence

ORD record
ord-ae506f3349714a41aea7a3f6aed526cf
Source dataset
uspto-grants-1989_12
Patent number
US04885306

Reaction notes

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