Synthesis of high-specific activity tritium and optically pure [14C]CP-101,606. Enantioselective crystallization of a radiochemically racemic mixture
Autor: | K. E. McCarthy, S. A. Miller, M. L. Dumont, J. Z. Stemple, Bertrand L. Chenard, Butler Todd W |
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Rok vydání: | 1997 |
Předmět: |
chemistry.chemical_classification
Ketone Chemistry medicine.drug_class Organic Chemistry Enantioselective synthesis Alkylation Biochemistry Analytical Chemistry Aminoketone Sodium borohydride chemistry.chemical_compound Hydrogenolysis Drug Discovery medicine Organic chemistry Racemic mixture Radiology Nuclear Medicine and imaging Enantiomer Spectroscopy |
Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 39:973-985 |
ISSN: | 0362-4803 |
Popis: | The syntheses of racemic, high-specific activity tritium and optically pure, carbon-14 labelled CP-101,606 is described. The tritium labelled material was prepared at 35.6 Ci/mmol by hydrogenolysis of the dibromo analog 5. In the carbon-14 synthesis, the radiolabel was introduced in the final carbon-carbon bond forming step by alkylation of the readily available aminoketone 8 with [14C]methyl iodide. Threo-selective sodium borohydride reduction of the ketone and deprotection of the phenol gave racemic [14C]CP-101,606. Enantiomerically pure (+)-[14C]CP-101,606 was obtained by addition of optically pure, unlabelled drug and directly recrystallizing the enantiomerically enriched, but radiochemically racemic, mixture. © 1997 John Wiley & Sons, Ltd. |
Databáze: | OpenAIRE |
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