(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid → (4R)-2-(2-Hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidinecarboxylic acid

HRID 851739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851739
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@H:18]([C:19]([OH:21])=[O:20])[CH2:17][S:16][CH:15]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])=[O:13])(=O)C1C=CC=CC=1>N>[OH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH:15]1[N:14]([C:12](=[O:13])[CH2:11][CH2:10][SH:9])[C@H:18]([C:19]([OH:21])=[O:20])[CH2:17][S:16]1

Komponenten

3

Edukt 1

HCID 12915688(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

Produkt 1

HCID 13019472(4R)-2-(2-Hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

To 4.2 g of (4R)-3-(S-benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 40 ml of conc. ammonia is added and this solution is stirred at room temperature for 1 hour. Excess ammonia is removed in vacuo and the by-product, benzamide, is extracted with ethyl acetate. The aqueous layer is acidified with dilute hydrochloric acid and the produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness in vacuo to give the titled compound, yield 2.2 g (70%), mp. 146°-148° C. (ethyl acetate), [α]D26 +176° (c=1.0, methanol).

Aufarbeitung

  1. customExcess ammonia is removed in vacuo
  2. extractionthe by-product, benzamide, is extracted with ethyl acetate
  3. extractionthe produced oil is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5fbca6383abd4638abf27cd8b5b9c4be
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386096

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