Resolution of Double Salts via Crystallization-Induced Diastereomeric Transformation (CIDT)
Corresponding Author
Melba Simon
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
E-mail: [email protected]
Search for more papers by this authorSophie Shortt
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorConor Burke
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorEóin Bourke
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorAnita Umerska
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorAngel Jacob
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorSharon Davin
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorBrian Glennon
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorCorresponding Author
Melba Simon
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
E-mail: [email protected]
Search for more papers by this authorSophie Shortt
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorConor Burke
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorEóin Bourke
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorAnita Umerska
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorAngel Jacob
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorSharon Davin
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorBrian Glennon
APC Ltd., Building 11, Cherrywood Business Park, Dublin, D18 DH50 Ireland
Search for more papers by this authorAbstract
The efficient enantioseparation of racemic compounds remains a critical challenge in pharmaceutical manufacturing. This investigation examines the crystallization-induced diastereomeric transformation (CIDT) of (S)-ketoprofen-(S)-phenylethylamine salts as a strategy for obtaining high-purity diastereomeric salts. Solubility phase diagrams were constructed for diastereomeric salts. A double salt system was identified, and a solvent system of 2-propanol and heptane (50:50 wt.%) was optimal for crystallization. Among the seven base catalysts screened, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) was found to be the most effective. Optimization studies demonstrated that 5–10 mol% DBU provides the highest purity (98.8 %) with 26.2 % yield. These results provide insights into the dual role of DBU as a catalyst (forming mixed salts) and cosolvent, influencing yield. The findings highlight CIDT as a robust method for the enantioseparation of diastereomeric salts in pharmaceutical applications.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
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