ENANTIOSELECTIVE PROCESS FOR PRODUCING 1-.BETA.-METHYLCARBAPENEM ANTIBIOTIC INTERMEDIATES

• Main Authors: SHINKAI, ICHIRO, FUENTES, LELIA M, SALZMANN, THOMAS N
• Format: Patent
• Language: English; French
• Published: 29.06.1993
• Edition: 5
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS; THEIR RELEVANT APPARATUS; TRANSPORTING

3326P/0716A 3327P/l006A 17179Y TITLE OF THE INVENTION ENANTIOSELECTIVE PROCESS FOR PRODUCING l-BETA-METHYLCARBAPENEM ANTIBIOTIC INTERMEDIATES A process is described for the stereocontrolled synthesis of intermediates useful in producing l-betamethylcarbapenem antibiotic An example of a compound prepared by the process of the present invention, would be a compound of Formula II: (II) wherein X1 and X2 are independently O or S, R1 is C1-C4 lower alkyl or alkoxyl, R2 and R9 are independently selected from hydrogen, C1-C4 linear, branched or cyclic alkyl, unsubstituted or substituted with fluoro, hydroxy, or protected hydroxy, with the proviso that both R2 and R9 are not unsubstituted alkyl, R3 is H or easily removable protecting group, R4, R5 and R6 are independently selected from H, C1-C4 alkyl, C7-C10 aralkyl, C6-C10 aryl, C7-C10 alkaryl, whlch can be substituted with -OH, -OR10, -SH, -SR10, where R10 is C1-C4 alkyl, with the proviso that R4 and R5 are not identical.