Penicillamine → 4-Thiazolidinecarboxylic acid, 2-(2-(dimethylamino)-2-oxoethyl)-2,5,5-trimethyl-

HRID 434548

Reaction equation

HRID 434548 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH3:10][N:11]([CH3:18])[C:12](=[O:17])[CH2:13][C:14]([CH3:16])=O.S([O-])([O-])(=O)=O.[Mg+2]>C1C=CC=CC=1>[CH3:4][C:3]1([CH3:5])[S:6][C:14]([CH2:13][C:12]([N:11]([CH3:18])[CH3:10])=[O:17])([CH3:16])[NH:1][CH:2]1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 5852PenicillamineHCID 16278DimethylacetoacetamideHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 30699314-Thiazolidinecarboxylic acid, 2-(2-(dimethylamino)-2-oxoethyl)-2,5,5-trimethyl-Yield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 2.00 g (13.4 mmoles) of D-penicillamine and 1.73 g (13.4 mmoles) of N,N-dimethylacetoacetamide in 15 ml of dry benzene, and 0.6 g of anhydrous magnesium sulfate was refluxed for 3.5 hours under a stream of argon. The reaction mixture became clear and then the solvent was distilled off. The resulting residue was dissolved in hot methyl alcohol. Insolubles were removed by filtration and the solvent was again distilled off. The residue was crystallized from chloroform and further recrystallized from ethyl alcohol-ether to give 2.3 g of 4-carboxy-2,5,5-trimethylthiazolidine-2-N,N-dimethylacetamide as colorless prisms.

Workup

  1. temperaturewas refluxed for 3.5 hours under a stream of argon
  2. distillationthe solvent was distilled off
  3. dissolutionThe resulting residue was dissolved in hot methyl alcohol
  4. customInsolubles were removed by filtration
  5. distillationthe solvent was again distilled off
  6. customThe residue was crystallized from chloroform
  7. customfurther recrystallized from ethyl alcohol-ether

Sources & evidence

ORD record
ord-dea7b4a90e8c42ab96f85ff15f067179
Source dataset
uspto-grants-1983_08
Patent number
US04398026

Linked notes

Loading…