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Synthesis, NMR analysis and applications of isotope-labelled hydantoins

Chapter 24. Radiochemistry

The syntheses of 3H- and 14C-label led S-(+)-6-fluoro-2,3-dihydrospiro-[4H-1-benzopyran-4,4′-imidazolidin]-2′,5′-dione (sorbinil, CP-45,634), an aldose reductase inhibitor with potential utility in the treatment of chronic diabetic complications, are described. Tritiated sorbinil was prepared by a reductive dehalogenation of the 8-chloro substituted analog with 3H2. 14C-labelled CP-45,634 was prepared using a Bucherer-Bergs synthesis of the racemic hydanto in beginning with 2,3-dihydro-6-fluoro-4H-1-benzopyran-4-one and 14C-potassium cyanide, followed by brucine resolution to isolate the pharmacologically active S-(+)-enantiomer.

Michael Evans

Papers

Synthesis of 2H-, 3H- and 14C-labelled CP-45,634 (sorbinil)