Cysteamine → 4-Oxo-4-[(2-sulfanylethyl)amino]butanoic acid

HRID 465894Notes

Reaction equation

HRID 465894 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1>O.[Zn]>[SH:4][CH2:3][CH2:2][NH:1][C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 6058CysteamineHCID 7922Succinic anhydride

Product 1

HCID 224508284-Oxo-4-[(2-sulfanylethyl)amino]butanoic acidYield 84.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5 g of cysteamine and 6 g of succinic anhydride is stirred under an inert atmosphere at a temperature of about 100° C. The transformation of the starting products is practically total one-half hour after the beginning of the reaction. The mixture is dissolved in 50 cm3 of water to which are added, with stirring, 5 g of sulfonic acid resin and 3 g of zinc powder to transform the disulfide present in the mixture. The resin is removed by filtration and the filtrate is concentrated under reduced pressure. After drying, 9 g of N-(2-mercapto ethyl) succinamic acid are obtained whose characteristics are identical to those of the acid obtained following the procedure of section (a), above.

Workup

  1. waitThe transformation of the starting products is practically total one-half hour
  2. customafter the beginning of the reaction
  3. additionare added
  4. stirringwith stirring
  5. customThe resin is removed by filtration
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customAfter drying

Sources & evidence

ORD record
ord-171af137619143c0bf8b219318a5d71a
Source dataset
uspto-grants-1992_10
Patent number
US05154918

Reaction notes

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