title: Practical synthesis of a 1beta-methylcarbapenem, J-111,225, using 4-mercapto-2-[4-(N-methylaminomethyl)phenyl]pyrrolidine as a precursor.
abstract: An effective and practical procedure for the synthesis of J-111,225 (1), a new 1beta-methylcarbapenem, was developed using 4-mercapto-2-14-(N-methylaminomethyl)phenyl]pyrrolidine (2a) as a precursor. The coupling reaction of 2a with p-nitrobenzyl (PNB)-protected 1beta-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.
authors: Banyu Tsukuba Research Institute, Banyu Pharmaceutical Co., Ltd., Tsukuba, Ibaraki, Japan. imamrahk@banyu.co.jp
authors: H
authors: H
authors: Imamura
authors: A
authors: A
authors: Shimizu
authors: H
authors: H
authors: Sato
authors: Y
authors: Y
authors: Sugimoto
authors: S
authors: S
authors: Sakuraba
authors: K
authors: K
authors: Yamada
authors: H
authors: H
authors: Morishima
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D015780:Carbapenems / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: C432959:4-mercapto-2-(4-(N-methylaminomethyl)phenyl)pyrrolidine; D000890:Anti-Infective Agents; D015780:Carbapenems; D007202:Indicators and Reagents; C404721:J 111225; D011759:Pyrrolidines