1380110-38-2Relevant academic research and scientific papers
Process Development for the Synthesis of Monocyclic β-Lactam Core 17
Lall, Manjinder S.,Tao, Yong,Arcari, Joel T.,Boyles, David C.,Brown, Matthew F.,Damon, David B.,Lilley, Susan C.,Mitton-Fry, Mark J.,Starr, Jeremy,Stewart, Andrew Morgan,Sun, Jianmin
, p. 212 - 218 (2018)
Process development and multikilogram synthesis of the monocyclic β-lactam core 17 for a novel pyridone-conjugated monobactam antibiotic is described. Starting with commercially available 2-(2,2-diethoxyethyl)isoindoline-1,3-dione, the five-step synthesis features several telescoped operations and direct isolations to provide significant improvement in throughput and reduced solvent usage over initial scale-up campaigns. A particular highlight in this effort includes the development of an efficient Staudinger ketene-imine [2 + 2] cycloaddition reaction of N-Boc-glycine ketene 12 and imine 9 to form racemic β-lactam 13 in good isolated yield (66%) and purity (97%). Another key feature in the synthesis involves a classical resolution of racemic amine 15 to afford single enantiomer salt 17 in excellent isolated yield (45%) with high enantiomeric excess (98%).
MONOBACTAMS
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Page/Page column 85-86, (2012/06/16)
The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.
