✦ LIBER ✦

Synthesis of (5R,6S)-6-[(1R)-hydroxyethyl]-3-[1-methylpyridinium-2-YL-methanethio]-[3-14C]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

✍ Scribed by J. E. Swigor; C. U. Kim; K. A. Pittman

Publisher: John Wiley and Sons
Year: 1988
Tongue: French
Weight: 198 KB
Volume: 25
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580250604

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✦ Synopsis

The synthesis of the title compound (4) is described.

Treatment of (3S)-[(lR)-hydroxyethyl]-(4R)-

[ 3-(p-nitrobenzyloxy) carbonyl-2-0x0-[ 2-I4C] -3-diazopropan-l-yl]azetidin-2-one1 with rhodium diacetate achieved ring closure forming (5R,6S)-pnitrobenzyl-6-~(1R)-hydroxyethyl]-3,7-dioxo-[3-14C]-l-azabicyclo[ 3.2.0lheptane-2-carboxylate (1). Reaction with diphenylchlorophosphate followed by 2-(mercaptomethy1)pyridine under basic conditions produced (SR,6S)-p-nitrobenzyl-6-[(lR)-hydroxyethyl]-3-(pyridine-2-yl-me thanethio) -[ 3-I4C] -7-0x0l-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2). Formation of the quaternary compound with methyl fluorosulfonate and deprotecting the acid by hydrogenolysis gave the title compound (4) in 6% overall radiochemical yield.

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