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

HRID 905180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905180
[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-453bb3c7fff34ae1a26e7417dcd20889
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04423054

Notizen zur Reaktion

Wird geladen…