Methyl mercapturate synthesis: an efficient, convenient and simple method.
A safe and simple method for methyl S-arylmercapturate synthesis is described. Thirteen such compounds, to be used afterwards in metabolism studies, have been obtained with yields ranging from 71 to 99.6%. These compounds were obtained using a sulfa-Michael addition and synthesized by adding the corresponding thiophenols to a mixture composed of methyl 2-acetamidoacrylate (MAA), potassium carbonate and a phase transfer catalyst, Aliquat 336. MAA, the initial synthon, was itself isolated in quasi quantitative yield following a fully described synthesis.
Cossec
Benoît
B
Institut National de Recherche et de Sécurité, Département Polluants et Santé, Rue du Morvan CS 60027, Vandoeuvre, 54519 cedex, France. benoit.cossec@inrs.fr
Cosnier
Frédéric
F
Burgart
Manuella
M
D000111:Acetylcysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000179:Acrylates; D002254:Carbonates; D008660:Metabolism; D010636:Phenols / Q000737:chemistry; D011188:Potassium; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000179:Acrylates; D002254:Carbonates; D010636:Phenols; D013438:Sulfhydryl Compounds; C011392:N-acetyldehydroalanine methyl ester; C042983:thiophenol; C037593:potassium carbonate; D011188:Potassium; D000111:Acetylcysteine