Amino acid modifications: lab scale-up

The question of late-stage modification of amino acid residues is the kind of stuff that interests a lot of people. In this regard, it is exciting to see studies in which C-H activation is accomplished in meaningful contexts, which to me implies that such reactions tolerate fairly polar amide functionalities. I am really interested in the chemistry that recently came out of John Hartwig’s lab at Berkeley. This is the kind of C-H activation I enjoy reading about because it is also scalable. To prove my point, here is an implementation of this methodology by Keith James and co-workers at the Ferring Research Institute in California. I heard Keith speak about this process during the ACS meeting in Dallas last Spring. The multigram scale on display here is what’s particularly impressive. As Tony Montana (from “Scarface”) would say: “That I like!”. The reason there is a need to block one of the meta positions in the starting material is to avoid low selectivity, of course. This is a powerful transformation and I wish there were more examples of scalable C-H reactions of this kind…


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