Synthesis of [14C]‐labelled tolrestat(N‐[[5‐(trifluoromethyl)‐6‐methoxy‐1‐naphthalenyl]‐[14C]thioxomethyl]‐N‐methylglycine; AY‐27, 773)
- 1 March 1984
- journal article
- research article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 21 (3) , 229-235
- https://doi.org/10.1002/jlcr.2580210305
Abstract
[14C]‐Tolrestat(N‐[[5‐(trifluoromethyl)‐6‐methoxy‐1‐naphthalenyl]‐[14C]‐thioxomethyl]‐N‐methylglycine; [14C]AY‐27, 773), a new aldose reductase inhibitor, was prepared by incorporating [14C]carbon dioxide. The intermediate, 6‐methoxy‐5‐trifluoromethyl‐[1–14C]‐naphthoic acid, prepared by carbonation of the corresponding lithiated derivative, was condensed with sarcosine methyl ester hydrochloride, converted to the thioamide and hydrolyzed. [14C]Tolrestat, having a specific activity of 52.7 μCi/mg was obtained in 26% overall yield from [14C]barium carbonate and had a radiochemical purity of 97%.Keywords
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