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Synthesis of 14C-labelled leukotriene receptor antagonists: 5-Substituted-4,6-dithianonanedioic acid derivatives

✍ Scribed by George Y. Kuot; Richard H. Dewey; John F. Newton; Carl D. Perchonock; Mary E. McCarthy

Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
452 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two lqC-labelled leukotriene receptor antagonists were prepared from two aryl bromides and potassium [ 14C]cyanide. cyanide was converted to copper(1) [L4C]cyanide and was subsequently used to displace the bromine atom from two dry1 bromides, 2-dodecylbromobenzene and 2-(8-phenyloctyl)bromobenzene. The resulting nitriles were reduced to aldehydes with diisobutylaluminum hydride and the aldehydes were reacted with 3-mercaptopropionic acid to give 5-(2-dodecylphenyl)-4,6-dithianonanedioic acid ( I 'C-SKSF 102081) and 5-[2-(8-phenyloctyl)phenyl]-4,6-dithianonanedioic acid ( "C-SKSF 1029221, respectively. in about 30% overall yield with radiochemical purity of greater than 95%. Their structures were assigned based on the analytical data of the corresponding nonradiolabelled compounds obtained from the nonradioactive preparations.

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