1229617-70-2Relevant academic research and scientific papers
A practical synthesis of 5-lipoxygenase inhibitor MK-0633
Gosselin, Francis,Britton, Robert A.,Davies, Ian W.,Dolman, Sarah J.,Gauvreau, Danny,Hoerrner, R. Scott,Hughes, Gregory,Janey, Jacob,Lau, Stephen,Molinaro, Carmela,Nadeau, Christian,Oshea, Paul D.,Palucki, Michael,Sidler, Rick
, p. 4154 - 4160 (2010)
Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesulfonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).
