95336-26-8Relevant academic research and scientific papers
Total Synthesis of Analogues of the β-Lactam Antibiotics. Part 4. 4-t-Butoxycarbonyl-8-oxo-1,3,4-triazabicyclooct-2-ene-2-carboxylates
Pant, Chandra M.,Stoodley, Richard J.,Whiting, Andrew,Williams, David J.
, p. 297 - 302 (2007/10/02)
t-Butyl hydroxy(4-iodomethyl-2-oxoazetidin-1-yl)acetate (6a) was transformed into t-butyl 4-t-butoxycarbonyl-8-oxo-1,3,4-triazabicyclooct-2-ene-2-carboxylate (9a) by sequential reactions involving thionyl chloride , t-butyl carbazate , and silver(I) oxide.In the last reaction, the 2-t-butoxycarbonylhydrazonoacetate (18a) is a likely intermediate.The structure of compound (9a) was supported by its conversion into methyl 1-t-butoxycarbonyl-3-methoxycarbonyl-1,4,5,6-tetrahydro-1,2,4-triazin-5-ylacetate (11b) by the action of sodium hydroxide followed by iodomethane, and confirmed by a single crystal X-ray analysis.The p-nitrobenzyl and benzyl esters of the triazabicyclo-octene, i.e. compounds (9c,d), were prepared from the carbinols (6b,c) by a similar reaction sequence.Hydrogenolysis of the benzyl ester (9d) gave the acid (9b), the sodium salt of which lacked antibacterial activity.
