Hydrochloric Acid → (4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid

HRID 223704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 223704
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:22]([S:30][CH2:31][C@H:32]([CH3:36])[C:33](Cl)=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O>[C:22]([S:30][CH2:31][C@@H:32]([CH3:36])[C:33]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2825743(4R)-2-(4-methylphenyl)-1,3-thiazolidine-4-carboxylic acidHCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chloride

Produkt 1

HCID 12915626(4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4.5 g of (4R)-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid and 4.3 g of sodium carbonate are dissolved in 25 ml of water and 4.9 g of (2S)-S-benzoyl-3-mercapto-2-methylpropanoyl chloride is added dropwise while stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 1 hour and acidified with dilute hydrochloric acid. The produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to dryness in vacuo to give oil. The produced oil is purified by silica gel column chromatography to give the titled compound, yield 4.0 g (48%), mp. 131°-132° C. (ethyl acetatehexane), [α]D26 +117.6° (c=1.0, methanol).

Aufarbeitung

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. temperaturecooling for 1 hour
  5. extractionThe produced oil is extracted with ethyl acetate
  6. washThe ethyl acetate layer is washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customto give oil
  10. customThe produced oil is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c53acea2ba8440c0ac34ecaa4ac442c2
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04356183

Notizen zur Reaktion

Wird geladen…