Project Goal:

Custom synthesis of three complex heterocyclic compounds for a customer

Details:

Synthesis of each target molecule involved a multistep sequence.  For two of the compounds, the available literature procedures, which were performed with mg scale, were modified to suit the large scale synthesis of the target compounds on the multi – gram scale.

 
As for compound three, which was a highly polar molecule containing multi-functional groups, there was no specific literature procedure. A synthetic protocol involving a seven-step sequence was applied to synthesize this compound utilizing the common functional group manipulations known in the literature.

Outcomes:

The requested quantities of all three molecules were synthesized in good yields and with purities higher than expected.  In addition, HPLC method development resulted in identifying suitable conditions to monitor the reactions and assess the purity of the intermediates and final compounds.  Suitable purification methods were established to purify highly-polar water soluble components of the syntheses by crystallization or normal phase column purifications verses the reverse phase purifications, which were applied to similar molecules in literature.  The final step of the synthesis for the third molecule required a serious route scouting to avoid the formation of a major byproduct.  This study was successfully completed and resulted in identifying suitable conditions to fully suppress this side reaction.   All the work was accomplished in 10 weeks.