新产品编号:1669519

Chemical Name: (1R,5S,6S)-2-[5(S)-[3(S),4(S)-Dihydroxypyrrolidin-1-ylcarbonyl]pyrrolidin-3(S)-ylsulfanyl]-6-[1(R)-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid
项目整合开发状态: Preclinical
项目研究机构: Korea Inst. Sci. Technol. (Originator), Korea Res. Inst. Chem. Technol. (Originator)
合成路线:L-Tartaric acid (I) was converted to succinimimide (II) upon treatment with benzylamine in refluxing xylene with azeotropic removal of water.Subsequent reduction of (II) with borane,generated from NaBH4 and BF3,afforded pyrrolidine (III).Removal of the N-benzyl group of (III) was effected by hydrogenolysis over Pd/C,and the resulting secondary amine (IV) was coupled with the N-protected 3-thioacetylproline (V) to furnish amide (VI).Deacetylation of (VI) under basic conditions provided thiol (VII).Condensation of thiol (VII) with carbapenem enolphosphate (VIII) afforded thioether (IX).The 4-nitrobenzyl protecting groups of (IX) were finally removed by hydrogenolysis over Pd/C.