[Synthesis and study of the properties of (3S-trans)-3-amino-4-methylmonobactamic acid]. / Sintez i izuchenie svoistv (3S-trans)-3-amino-4-metilmonobaktamovoi kisloty.

ABSTRACT

The process for production of (3S-trans)-3-amino-4-methylmonobactamic acid (3-AMMA) was studied. It included transformation of L-threonine into amide, protection and activation of the functional groups, cyclization of the resulting beta-mesyloxyacylsulfomate into azetidinone followed by removal of the protecting group. For estimation of the completeness of the process separate stages and their optimization chromatography and spectroscopy were used. Stability, optical activity and chromatographic mobility of 3-AMMA under various conditions were studied. It was shown that solutions of 3-AMMA were rather stable in weak acid and neutral media and degraded at pH greater than 9.0. Control of this process was provided by circular dichroism.