3-SUBSTITUTED-7-OXO-1-AZABICYCLO[3,2,0]HEPT-2-ENE-2-CARBOXYLATE COMPOUNDS

摘要

PURPOSE: Provided is 3-Substituted-7-oxo-1-azabicyclo£3.2.0|hept-2-en-2-carboxylate derivatives and their preparation method, wherein the derivatives are used as an intermediate for preparing the carbapenem antibiotics. CONSTITUTION: The 3-substituted-7-oxo-1-azabicyclo£3.2.0|hept-2-en-2-carboxylate derivatives are represented by the formula 1, wherein R2 is H or an alkyl group of low molecular weight; R3 is a carboxy-protecting group; and R4 and R5 are independent each other and are an alkyl group of low molecular weight. The compounds of the formula 1 is prepared by reacting the compound of the formula 12a and the triazine derivative of the formula 13, wherein R2 is H or an alkyl group of low molecular weight; R3 is a carboxyl protecting group; R4 and R5 are independent each other and are an alkyl group of low molecular weight; and Hal represents a halogen atom. Preferably the reaction is carried out in the presence of a base, preferably selected from N-methylmorpholine, morpholine and pyridine, in an organic solvent selected from dichloromethane, chloroform, acetonitrile, tetrahydrofuran, dimethylformamide, dimethylacetamide, tetramethylenesulfone, hexamethylphosphoramide and their mixtures, and at the temperature of -50 to 100 deg.C.