Reaktion #954601

ord-de81d460f1c5428fb0b7238070f16668

Reaktionsgleichung

O=Cc1ccc(O)cc1
4-hydroxybenzaldehyde
CC(C)(S)[C@@H](N)C(=O)O
D-penicillamine
→
CC1(C)SC(c2ccc(O)cc2)N[C@H]1C(=O)O
title acid
CC1(C)SC(c2ccc(O)cc2)N[C@H]1C(=O)O
5,5-Dimethyl-2-(4-hydroxyphenyl)-thiazolidine-4(S)-carboxylic acid

Edukte

O=Cc1ccc(O)cc1
4-hydroxybenzaldehyde
CC(C)(S)[C@@H](N)C(=O)O
D-penicillamine

Reagenzien

Keine

Lösungsmittel

CO
methanol
CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONare added to a solution
  2. 2
    Sonstigerecrystallization from ethanol
  3. 3
    workup.ADDITIONcontaining water

Vorschrift

1.26 g (10 mmoles) of 4-hydroxybenzaldehyde dissolved in 20 ml of 30% aqueous methanol are added to a solution containing 1.49 g (10 mmoles) of D-penicillamine in 30 ml of 30% methanol. After stirring for 20 hours and recrystallization from ethanol containing water, the title acid is obtained in a yield of 2.4 g (94.8%), m.p.: 207°-209° C., [α]D =+91.3° (c=0.2, dimethylformamide).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04775675uspto-grants-1988_10