Cystamine → 1-(2-Sulfanylethyl)pyrrolidine-2,5-dione

HRID 465895

Reaction equation

HRID 465895 reaction equation
C1(=O)OC(=O)CC1.[SH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O.NCCS.NCCSSCCN>O>[SH:8][CH2:9][CH2:10][N:11]1[C:12](=[O:18])[CH2:13][CH2:14][C:15]1=[O:17]

Participants

6

Reactant 4

HCID 2915CystamineHCID 6058CysteamineHCID 7922Succinic anhydrideHCID 224508284-Oxo-4-[(2-sulfanylethyl)amino]butanoic acid

Product 1

HCID 220163571-(2-Sulfanylethyl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About one-half hour is necessary for the complete transformation of the succinic anhydride (V.P.C.). At this stage, to facilitate the cyclization reaction, the reaction mixture is placed under reduced pressure and the evolution of the reaction mixture is followed by acidimetric dosage of the nontransformed N-(2-mercapto ethyl) succinamic acid. At the end of the reaction, the mixture is cooled and 7 g of crude product are obtained and dissolved in 50 cm3 of water to which are added, with stirring, 10 g of sulfonic acid resin. After stirring for one hour, the resin, having fixed the traces of cysteamine or cystamine not having reacted, is removed by filtration. To reduce the disulfide optionally present, there are added to the stirred filtrate, 10 g of sulfonic resin and 3 g of zinc powder. After 3 hours the mixture is filtered and the filtrate is concentrated under reduced pressure. After drying, 5 g of N-(2-mercapto ethyl) succinimide are obtained in the form of a white powder whose melting point is 45° C.

Workup

  1. customthe cyclization reaction
  2. customAt the end of the reaction
  3. temperaturethe mixture is cooled
  4. custom7 g of crude product are obtained
  5. additionare added
  6. stirringAfter stirring for one hour
  7. customhaving reacted
  8. customis removed by filtration
  9. additionthere are added to the stirred filtrate, 10 g of sulfonic resin and 3 g of zinc powder
  10. filtrationAfter 3 hours the mixture is filtered
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. customAfter drying

Sources & evidence

ORD record
ord-9850519c0bec4d40b7c2d8c2e22ba1c0
Source dataset
uspto-grants-1992_10
Patent number
US05154918

Linked notes

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