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

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Reaction Steps

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)].

Provenance & Evidence