PROCESS FOR STEREOSELECTIVE PREPARATION OF 4-BMA USING A CHIRAL AUXILIARY

• Main Authors: MOON, SEONG CHEOL, SONG, CHUNG HYUN, HAN, CHANG WOAN, HA, HYUN JOON, SHIN, DONG GYUN, LEE, WON KOO, LEE, BYUNG GOO, SONG, YOON SEOK, HONG, MYENG CHAN, LEE, KYUNG HO, KIM, JONG HYEK
• Format: Patent
• Language: English; French
• Published: 23.10.2008
• Subjects: CHEMISTRY; CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION ORPROCESSING OF GOODS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINSTCLIMATE CHANGE

The present invention relates to a process for preparing (3R,4S)-3-[[[R]-V-t- butyldimethylsilyloxy] ethyl] -4- [(/?)- l"-carboxyethyl]-2-azetidinone [4-BMA: formula (6)], a key intermediate for the synthesis of carbapenem and penem antibiotics. Specifically, the present invention relates to a process comprising first, the preparation of a chiral auxiliary from cheap L-Valinol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild conditions. L'invention porte sur du (3R,4S)-3-[[[R]-V-t- butyldiméthylsilyloxy] éthyl] -4- [(/?)- l"-carboxyéthyl]-2-azétidinone] 4-BMA, de formule (6), intermédiaire de synthèse des antibiotiques carbapénem et pénem, et spécifiquement, sur un procédé consistant d'abord, à préparer un auxiliaire chiral du L-Valinol bon marché, puis à préparer le 4-BMA avec un fort rendement et une haute sélectivité, dans des conditions industrielles douces.