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Synlett 1999; 1999(S1): 909-912
DOI: 10.1055/s-1999-3111
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Trials for the Synthesis of (R)-4-Mercapto-pyrrolidin-2-one ((R)-MPD)

Satoshi Kobayashi* , Katsuhiro Kobayashi, Koichi Hirai
  • *Process Development Laboratories, Sankyo Co., Ltd. No. 173, Nakahara-Kamijuku, Hiratsuka-shi, Kanagawa 254-0071, Japan; Fax +81(4 63)31 65 25; E-mail: khirai@hira.sankyo.co.jp
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Publication History

Publication Date:
31 December 1999 (online)

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Several trials were made for the syntheses of (S)-4-hydroxy-pyrrolidin-2-one ((S)-HPD) and (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD), a substituent at the 2-position of the orally active carbapenem antibiotic CS-834. The latter was synthesized from prochiral dimethyl or diethyl 3-p-methoxybenzylthioglutarate using pig liver esterase technology to give monoester with an optical purity of 51-71% e.e. as a key intermediate.

γ-lactam formation - 4-mercapto-pyrrolidone - pig liver esterase - intramolecular Schmidt reaction - Curtius rearrangement - 4-hydroxy-pyrrolidone - CS-834

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