Hydrochloric Acid → (4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

HRID 905182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905182
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:21][CH2:22][C:23](Cl)=[O:24].[C:26]([O-:34])(=[S:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[K+].Cl>O>[C:26]([S:33][CH2:21][CH2:22][C:23]([N:10]1[C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:24])(=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 6710826(R)-2-Thiophen-2-ylthiazolidine-4-carboxylic acidHCID 23681850Potassium thiobenzoate

Produkt 1

HCID 12915812(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

10.6 g of (4R)-2-(2-thienyl)-4-thiazolidinecarboxylic acid and 10.6 g of sodium carbonate are dissolved in 100 ml of water and 8.6 g of 3-bromopropanoyl chloride is added dropwise while stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 2 hours. To this reaction solution, 8.8 g of potassium thiobenzoate is added and stirred at room temperature for 1 hour. The solution is acidified with dilute hydrochloric acid and 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 in vacuo to give the titled compound, yield 11.6 g (57%), mp. 141°-143° C. (benzene), [α]D25 +107.7° (c=1.0, methanol).

Aufarbeitung

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. temperaturecooling for 2 hours
  5. stirringstirred at room temperature for 1 hour
  6. extractionthe produced oil is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b8e3795268d423c83ea5e5df9d61b41
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04423054

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