Sutezolid
M4ALL made improvements to the synthesis of a key intermediate of sutezolid which could lower raw material costs of the API by 45%-55%.
Key Assumptions
- The cost reductions of the M4ALL route are primarily driven by utilizing the commodity diethanolamine as a starting material rather than high-cost thiomorpholine and by eliminating the need for palladium catalysis that greatly affected the cost of the baseline route. The raw material cost reduction of the M4ALL route significantly depends on the market price of palladium.
- The baseline route was shared confidentially with the M4ALL team.
Improved Process to Prepare a Key Intermediate in the Synthesis of Sutezolid
Supplementary Materials for Process Development Work on Sutezolid Intermediate
Alternative Synthesis of Thiomorpholine Intermediate
Route Improvements
- Developed a route that leveraged the commodities diethanolamine and sodium sulfide as starting materials which were used to build the aryl thiomorpholine moiety. The baseline route, which starts with thiomorpholine directly, is much higher cost due to the high cost and low availability of thiomorpholine.
- Eliminated palladium catalyst which was the second biggest cost-driver of the baseline route.
- Made significant improvements to impurity profile. The most impactful impurity, a morpholino derivative, was reduced to <1 % (HPLC)
Additional M4ALL Sutezolid Publications
A Tandem Ring Closure and Nitrobenzene Reduction with Sulfide Provides an Improved Route to an Important Intermediate for the Anti-Tuberculosis Drug Candidate Sutezolid