Nonracemic Synthesis of GK−GKRP Disruptor AMG-3969

Hi Folks, it was a busier week than normal and I finally got a chance to work on a post.  There is no witty title here, either.  I couldn’t think of one.  I wanted to find something with some structures to draw because I haven’t posted anything of that nature in a while.  I originally thought I found a process development paper in JOC, but I was in  error.  I decided to post about it anyways, because it hits on some points that process chemists will identify with.

The post can be found in J. Org. Chem. 2014, 79, 3684−3687, doi: 10.1021/jo500336e.  Lead author is Matthew P. Bourbeau and colleagues at Amgen.  The paper is about the rework of an API synthesis.  The original synthesis was used to produce material but when your final product is racemic and being separated using SFC or SMB chromatography at the final step, it…