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I worked out a route to a synthetic intermediate, a protected amino acid bearing a bromomethylketone (I can use it to make a couple of potential inhibitors). My first route required the use of reagents that are too toxic for my circumstances, and I am researching alternatives before starting. One possibility is to convert a commercially available alkene into a bromomethylketone. I found a one-pot method that employs, OxoneR
, NBS, and modified IBX. The method uses "in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid." This method tolerates methyl esters.
My preferred protecting groups are BOC and tertiary
-butyl ester on the nitrogen and carboxylic acid respectively. To use this transformation, I suspect would have to buffer the OxoneR
or find a different protecting scheme. An alternative is to form a bromohydrin from the alkene, then find a suitable oxidant in the subsequent step. Thoughts?