Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry
Facile Synthesis of (R)-4-Mercaptopyrrolidine-2-thione from L-Aspartic Acid
Masahiko SEKIToshiaki SHIMIZU
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2001 年 65 巻 4 号 p. 973-976

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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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© 2001 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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