Practical Synthesis of a 1β-Methylcarbapenem, J-111, 225, Using 4-Mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine as a Precursor

Hideaki IMAMURA; Aya SHIMIZU; Hiroki SATO; Yuichi SUGIMOTO; Shunji SAKURABA; Koji YAMADA; Hajime MORISHIMA

doi:10.1248/cpb.49.476

Notes

Practical Synthesis of a 1β-Methylcarbapenem, J-111, 225, Using 4-Mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine as a Precursor

Hideaki IMAMURA, Aya SHIMIZU, Hiroki SATO, Yuichi SUGIMOTO, Shunji SAKURABA, Koji YAMADA, Hajime MORISHIMA

著者情報

キーワード: 1β-methylcarbapenem, J-111,225, non-protected side-chain thiol, practical synthesis

ジャーナルフリー

2001 年 49 巻 4 号 p. 476-479

DOI https://doi.org/10.1248/cpb.49.476

詳細

抄録

An effective and practical procedure for the synthesis of J-111, 225 (1), a new 1β-methylcarbapenem, was developed using 4-mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine (2a) as a precursor. The coupling reaction of 2a with p-nitrobenzyl (PNB)-protected 1β-methylcarbapenem enolphosphate 3a and successive removal of PNB group afforded J-111, 225 (1) in significantly increased yield compared to the ordinary procedure using a C-2 side-chain thiol with amino-protective groups.

責任著者(Corresponding author)

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