With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.915095-89-5,(S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran,as a common compound, the synthetic route is as follows.
915095-89-5, To the solution of (S)-3-(4-(5-bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran in tetrahydrofuran n-BuLi (2.5 mol) in hexane added at a rate that maintained the reaction temperature below -90C followed by addition of 2,3,4,6-tetra-0-trimethylsilyl-P-D- glucolactone in toluene at a rate that maintained the reaction temperature below -90C. The solution was stirred for 30 min at -95C prior to quenching by addition of methanol containing methanesulfonic acid. The reaction mixture was stirred overnight as the temperature raise to 20C. After completion of reaction, the reaction was quenched by the addition of triethylamine and distilled it out under vacuum. To the obtained residue water was added and extracted thrice with ethylacetate. The combined ethylacetate fractions were washed with brine and dried over sodium sulfate. The reaction mixture was concentrated to provide formula C in the form oil. To the methylenechloride solvent, aluminum chloride was added in one lot and cooled the mass to the temperature 0C to 10C. To the prepared solution acetonitrile was added followed by addition of triethyl silane at a rate such that the temperature was maintained between 0C to 10C. Mixed the above prepared complex with oil of formula C and stirred for 2 h. When HPLC analysis revealed that the reaction was completed, the reaction was quenched by addition of 50% aqueous hydrochloric acid solution. Aqueous layer was extracted with methylenechloride. Combined organic layer washed with 5% aqueous hydrochloric acid solution followed by water and brine. The organic layer was distilled and the obtained residue was added methylenechloride, acetic anhydride and dimethylaminopyridine, pyridine and stirred for 5-6 h. Water was added to the reaction mixture and layers were separated. The methylenechloride layer was distilled and ethanol was added to it followed by heating to 55-60C. The reaction mixture was cooled, filtered and dried to obtain acetylated empagliflozin of formula F.Yield: ~ 58%. Purity (by HPLC): >99.8%
The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; PIRAMAL ENTERPRISES LIMITED; GHARPURE, Milind; SHARMA, Sanjay Kumar; VISHWASRAO, Sandesh; VICHARE, Prasad; VARAL, Dipak; (24 pag.)WO2018/207111; (2018); A1;,
Tetrahydrofuran – Wikipedia
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