ENANTIOSELEKTIVES VERFAHREN ZUR HERSTELLUNG VON 1-BETA-METHYLCARBAPENEM- ANTIBIOTIKUMZWISCHENPRODUKTEN

• Main Authors: SHINKAI, ICHIRO, FUENTES, LELIA M, SALZMANN, THOMAS N
• Format: Patent
• Language: German
• Published: 15.07.1994
• 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

A stereo-controlled process is described for preparing a compound of the formula: wherein R is, e.g,. C1-C4 alkyl, R and R 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 R and R are not unsubstituted alkyl, and R is H or easily removable protecting group, comprising the steps of (a) reacting the compound: wherein L is a leaving group, with the chiral compound: wherein X and X are independently O or S, R is an easily removable enol protecting group, R and R and R are independently selected from H, C1-C4 alkyl, C7-C10 aralkyl, C6-C10 alkaryl, which can be substituted with -OH, -OR , -SH, -SR , where R is C1-C4 alkyl, with proviso that R and R are not identical, in the presence of an organic base and a Lewis acid catalyst to afford the compound: and then (b) contacting said compound in a solvent therefor, under basic hydrolysis conditions. This compound can be transformed into a carbapenem antibiotic.