Potassium Carbonate → (S)-2-acetylthio-3-phenylpropanoic acid

HRID 233368

Reaktionsgleichung

Reaktionsgleichung von HRID 233368
[C:1]([OH:4])(=[S:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14]>O.[OH-].[Na+]>[C:1]([S:3][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:4])[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11746403(R)-2-Bromo-3-phenylpropionic acidHCID 178418634HCID 178418634, Verbindung

Produkt 1

HCID 10176891(S)-2-acetylthio-3-phenylpropanoic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Thioacetic acid (9.3 cc) and potassium carbonate (7.5 g) in water (150 cc) are added under nitrogen atmosphere to a solution of (R)-2-bromo-3-phenylpropanoic acid (25 g) in 1M sodium hydroxide (110 cc). The solution is stirred for 15 hours at a temperature close to 20° C. After evaporation under reduced pressure, the residue is taken up with water and ethyl acetate. The aqueous phase is separated, acidified to pH=2 and then extracted with ethyl acetate. After washing, the organic phase is dried over sodium sulphate. After filtration and concentration under reduced pressure, (S)-2-acetylthio-3-phenylpropanoic acid (18.5 g) is obtained with a yield of 75% in the form of an oil having the following characteristics: Rf =0.49 [hexane/ethyl acetate/acetic acid (6:4:0.5 by volume)].

Aufarbeitung

  1. customclose to 20° C
  2. customAfter evaporation under reduced pressure
  3. customThe aqueous phase is separated
  4. extractionextracted with ethyl acetate
  5. washAfter washing
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. filtrationAfter filtration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13b55e1b2b834161b949f5f276cd2f4e
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591891

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