Electric Literature of 55357-38-5 ,Some common heterocyclic compound, 55357-38-5, molecular formula is C12H21NO4S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution comprising compound la prepared starting from 7.4 gr. of compound 2a a solution of 12.7 gr. of choline tosylate in dry acetonitrile was added. A solution of 5.9 ml. of triethylamine in 4 ml. DCM was added thereto. The reaction mixture was stirred overnight. The reaction mixture was then concentrated, 250 ml. of hexane was added and evaporated to dryness. The residue was redissolved in 390 ml. of THF and precipitated choline tosylate was filtered. Concentrated HCl (1. 7ml) was added and the reaction mixture was stirred for 1 hour. The reaction mixture was dried over magnesium sulfate, filtered, and the pH was basified with triethylamine. The precipitation was filtered, the filtrate was evaporated to dryness and then redissolved in a solvent mixture consisting of chloroform, methanol and water (8: 4: 3). The lower phase was separated and washed 4 times with the same upper phase and evaporated. The crude product was dissolved in 45 ml. of 1M tetrabutylammonium fluoride in THF and the reaction mixture was stirred at 45C for 2 hours. The resulting solution was evaporated and the crude product was purified by silicagel chromatographic column. (Eluent: gradual mounting concentration of methanol in chloroform). The relevant fractions were evaporated and the resulting product was then co-evaporated with acetonitrile. 1.49 of pure product was obtained (23% yield). 1H NMR 300 MHz (8 ppm, CD30D) : 0.92 (t, 3H), 1.31 (bm, 20H), 1.44 (m, 2H), 2.10 (q, 2H), 2.92 (m, 1H), 3. 33 (m, 1H), 3.67 (m, 2H), 3.92 (m, 1H), 4.04 (m, 2H), 4.30 (m, 2H), 5.55 (dd, 1H), 5. 78 (dt, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55357-38-5, its application will become more common.
Reference:
Patent; BIOLAB LTD.; WO2005/68480; (2005); A1;,
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