Add time:08/21/2019         Source:sciencedirect.com

Publisher SummarySulfones are sulfur derivatives of the general formula RSO2R' in which the sulfur atom is at an oxidation level between that of sulfoxides (RSOR') and sulfonic acids (RSO3H). This chapter describes the synthesis of S-benzyl-DL-α-methylcysteine sulfone from the corresponding sulfide; the procedure is generally applicable to the synthesis of amino acid and most other water-soluble sulfones. S-Benzyl-α-methylcysteine is prepared by the method of Potts in which 1-(benzylthio)-2-propanone is first synthesized from l-chloro-2-propanone and benzyl mercaptan, and that intermediate is then reacted with ammonium bicarbonate and sodium cyanide to form a hydantoin that can be hydrolyzed to the desired amino acid. S-Benzyl derivatives of amino acids that are available in thiol or disulfide form, for example, cysteine or homocystine, can be prepared directly by reaction with benzyl chloride. Benzyl chloride is a potent lacrimator and should be used in an exhaust hood. For thiol amino acids, the reaction should be carried out under nitrogen to avoid oxidation to the unreactive disulfide form. The cleavage of the S-benzyl group to yield α-methylcysteinesulfinic acid is also described. S-Benzyl-DL-α- methylcysteine sulfone (3.58 g, 13.9 mmol) is placed in a 500-ml three- necked round-bottomed flask and dissolved in 200 ml of liquid ammonia (the apparatus and procedure are as described above).

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