STEREOSELECTIVE PRODUCTION OF INTERMEDIATE USEFUL FOR PRODUCTION OF NEW CARBAPENEM, AND INTERMEDIATE

摘要

PROBLEM TO BE SOLVED: To obtain the subject new compound capable of being used as an intermediate for selectively synthesizing a new carbapenem derivative useful as an antibacterial agent in good yield. SOLUTION: The objective compound is pyrrolidine-4-thiol of formula I [(n) is an integer of 1-4) and obtained by reacting a derivative of formula II (R<1> is a lower alkylsulfonyl, etc.; R<2> is a protective group of an amino group) with a derivative of formula III [R<3> is a lower alkyl or an aryl; X is O atom or S atom. Y is azide or nitro; (m) is an integer of 2-5] to provide a derivative of formula IV as an intermediate, reducing the azido group or the nitro group of the derivative of formula IV to provide a lactam derivative of formula V, protecting the NH group of the formed cyclic amide, forming the protected cyclic amide into acylthio and deprotecting the protective group. The derivative of formula IV is also a new compound. Only the diastereomer with the objective configuration is enabled to be selectively obtained in good yield, when the new intermediate is used.