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- W2045486547 abstract "3-([2,6-14C]2-pyridinyldithio) propanoic acid, a disulphide covalent coupling reagent was synthesized in 12 steps from sodium [14C] cyanide. Condensation of sodium [14C] cyanide with 1,3-dibromopropane gave, after hydrolysis [1,5-14C] glutaric acid: 4 which was converted into [1,5-14C] glutarimide : 5 by heating at 280°C with anhydrous ammonia. The imide : 5 was then converted into [2, 6-14C] 2, 6-dichloropyridine: by 6 by treatment with phosphorous penta and trichlorides. Chlorine removal from 6 by hydrogen (Roney Nickel) gave [2, 6-14C] pyridine: 7 which was isolated as the hydrochloride. The latter was tranformed into [2, 6-14C] pyridine-N-oxide :11 by hydrogen peroxide treatment. 11 treated by acetic anhydride (15 hours - 130°C) rearranged into 2-acetyloxy [2, 6-14C] pyridine: 12 which was hydrolysed into [2, 6-14C] 2-pyridone: 13. Thiation of the latter by P2S5 in xylene gave 2-mercapto [2, 6-14C] pyridine: 10 which was then oxidized into [2, 6-14C] 2-dipyridinyldisuplphide: 14 the chlorination of which lead to [2, 6-14C] 2-pyridinylsulfenyl chloride: 15 which was not isolated. It was condensed with 3-mercapto propanoic acid to give 1 with an overall yield of 4% based on sodium cyanide - Specific activity was 55 mCi/mMol. The radiochemical purity checked by TLC and HPLC was 98.7%." @default.
- W2045486547 created "2016-06-24" @default.
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- W2045486547 date "1983-11-01" @default.
- W2045486547 modified "2023-09-23" @default.
- W2045486547 title "Synthese de L'Acide [Pyridinyl-2-(14C-2,6) Dithio]-3 Propanoique Reactif de Couplage Covalent" @default.
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- W2045486547 doi "https://doi.org/10.1002/jlcr.2580201105" @default.
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