HCID 19903350, compound → HCID 19903323, compound

HRID 2372372Notes

Reaction equation

HRID 2372372 reaction equation
[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH2:11]C)=[O:9]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OC)(=O)CC>[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 19903350HCID 19903350, compound

Product 1

HCID 19903323HCID 19903323, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 11124Methyl propionateSolvent

Procedure

To 4.5 g of ethyl 4-methyl-2-thioxopyrrolidine-3-carboxylate, were added 200 ml of methyl propionate and 7.0 ml of titanium tetraisopropoxide. The resulting mixture was heated under reflux for 3 days. After distilling off the excessive methyl propionate under reduced pressure, water and chloroform were added to the residue and insoluble matters were filtered off. The chloroform layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the chloroform, ethyl ether was added to the residue to thereby crystallize the same. Thus 2.2 g of the title compound was obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 days
  3. distillationAfter distilling off the excessive methyl propionate under reduced pressure, water and chloroform
  4. additionwere added to the residue and insoluble matters
  5. filtrationwere filtered off
  6. washThe chloroform layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  8. distillationAfter distilling off the chloroform, ethyl ether
  9. additionwas added to the residue
  10. customto thereby crystallize the same

Sources & evidence

ORD record
ord-4298b62038b94fd3be76049365d77d6d
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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