Facile synthesis of (R)-4-mercaptopyrrolidine-2-thione from L-aspartic acid |
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Authors: | Seki M Shimizu T |
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Affiliation: | Product & Technology Development Laboratory, Tanabe Seiyaku Co. Ltd., Osaka, Japan. m-seki@tanabe.co.jp |
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Abstract: | An SN2-type of substitution of (S)-bromide 4, which had been prepared from L-aspartic acid, with potassium thiobenzoate provided (R)-benzoylthio derivative 5 with complete inversion of the configuration. Compound 5 was converted, via iodide 6c, to (R)-4-amino-3-benzoylthiobutyric acid 8b. (R)-4-Mercapto pyrrolidine-2-thione 1 was readily obtained from 8b through cyclization with acetic anhydride, thionation with Lawesson's reagent and facile removal of the S-benzoyl group with sodium methoxide. |
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