The development of new synthetic methodology is an often overlooked necessity in the discovery stage of projects.
Chemistry is our core business, so your discovery projects will benefit from novelty as a result of synthetic method development.
In a recent collaboration with an ambitious biotech from Boston, the development of 5,6-dihydro[1,2,4]oxadiazine scaffolds required a sound synthetic method. It turned out that available chemistry was based on a small number of transformations with little scope and no control over stereochemistry.
Our discovery chemists investigated three new routes to the synthesis of the required oxadiazines in detail. Control over substituents at both the 3- and 5-positions of the scaffold was an important specification in the development study.
The most promising entry to enantiopure 5,6-dihydro[1,2,4]oxadiazine was a high-yielding condensation–cyclization strategy of diamines and imidates. The diamine building blocks are readily available from chiral amino acids to ensure control over the stereochemistry in the 5-position.
A short, but extensive, study advanced the project and revealed a new, widely applicable synthetic methodology.
This is yet another example of the impact of Mercachem discovery chemistry services on client projects!