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

HRID 434549

Reaktionsgleichung

Reaktionsgleichung von HRID 434549
C(Cl)(Cl)Cl.[NH2:5][C@@H:6]([C:11]([OH:13])=[O:12])[C:7]([SH:10])([CH3:9])[CH3:8].[CH3:14][N:15]([CH3:22])[C:16](=[O:21])[CH2:17][C:18]([CH3:20])=O>C(O)C>[CH3:8][C:7]1([CH3:9])[S:10][C:18]([CH2:17][C:16]([N:15]([CH3:22])[CH3:14])=[O:21])([CH3:20])[NH:5][CH:6]1[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 3

HCID 5852PenicillamineHCID 6212ChloroformHCID 16278Dimethylacetoacetamide

Produkt 1

HCID 30699314-Thiazolidinecarboxylic acid, 2-(2-(dimethylamino)-2-oxoethyl)-2,5,5-trimethyl-Ausbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 40 ml of a mixture of chloroform and ethyl alcohol (1:1) were suspended 1.49 g (10 mmoles) of D-penicillamine and 1.89 g (15 mmoles) of N,N-dimethylacetoacetamide. The suspension was heated at 80°-90° C. with stirring under a stream of argon to concentrate to a half its volume. 20 ml of a mixture of chloroform and ethyl alcohol (1:1) was added. The concentration and addition of the solvent were repeated until the reaction mixture turned completely clear and a small amount of insolubles was removed by filtration. The solvent was distilled off, and the resulting residue was treated according to the same procedure as in Example 1 to give 1.98 g of 4-carboxy-2,5,5-trimethylthiazolidine-2-N,N-dimethylacetamide as colorless prisms.

Aufarbeitung

  1. temperatureThe suspension was heated at 80°-90° C.
  2. concentrationto concentrate to a half its volume
  3. addition20 ml of a mixture of chloroform and ethyl alcohol (1:1) was added
  4. concentrationThe concentration and addition of the solvent
  5. customa small amount of insolubles was removed by filtration
  6. distillationThe solvent was distilled off
  7. additionthe resulting residue was treated

Quellen und Nachweise

ORD-Eintrag
ord-4a8b40ad07d84f5588416a1d95ebcd2d
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04398026

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