Penicillamine → 5,5-Dimethyl-2-(5-indanyl)-thiazolidine-4(S)-carboxylic acid

HRID 867411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867411
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH2:7][CH2:6]2)=O.[NH2:12][C@@H:13]([C:18]([OH:20])=[O:19])[C:14]([SH:17])([CH3:16])[CH3:15]>CO>[CH3:15][C:14]1([CH3:16])[S:17][CH:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[CH2:8][CH2:7][CH2:6]3)[NH:12][C@H:13]1[C:18]([OH:20])=[O:19]

Komponenten

4

Edukt 2

HCID 5852PenicillamineHCID 1216245-Indanecarboxaldehyde

Produkt 1

HCID 157250805,5-Dimethyl-2-(5-indanyl)-thiazolidine-4(S)-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.44 g (10 mmoles) of 5-formylindane are portionwise added to a solution containing 1.5 g of D-penicillamine in 100 ml of methanol at room temperature while stirring. After 48 hours, the mixture is evaporated to dryness. The residue is dissolved in ether with boiling, treated with activated carbon and filtered. The crude product is precipitated by adding petroleum ether. The thus-obtained product is dissolved in hot ethanol, clarified with carbon, filtered, then water is added up to a beginning opalescence. On cooling, the title compound precipitates in a crystalline form in a yield of 1.57 g (57.1%), m.p. 140°-142° C., [α]D20 =+18° (c=0.551, dimethylsulphoxide).

Aufarbeitung

  1. customthe mixture is evaporated to dryness
  2. dissolutionThe residue is dissolved in ether with boiling
  3. additiontreated with activated carbon
  4. filtrationfiltered
  5. customThe crude product is precipitated
  6. additionby adding petroleum ether
  7. dissolutionThe thus-obtained product is dissolved in hot ethanol
  8. filtrationfiltered
  9. additionwater is added up to a beginning opalescence
  10. temperatureOn cooling
  11. customthe title compound precipitates in a crystalline form in a yield of 1.57 g (57.1%), m.p. 140°-142° C., [α]D20 =+18° (c=0.551, dimethylsulphoxide)

Quellen und Nachweise

ORD-Eintrag
ord-bd6e5ffdb2eb452da36ddce8b7961ed3
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775675

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