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

HRID 223706

Reaktionsgleichung

Reaktionsgleichung von HRID 223706
[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

10.8 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-f90d061f8ab94a4db7b18efc0aee0b83
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04356183

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