As the paragraph descriping shows that 149809-43-8 is playing an increasingly important role.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.149809-43-8,((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.
To a solution of intermediate (Xla) (7.80 g, 25.1 mmol) in DMSO (60 mL) was added aq sodium hydroxide (3.0 mL, 12.5 M, 37.6 mmol). The mixture was stirred at RT for 10 min and was then treated portionwise with ((3S,5 )-5-((1 /-/-1 ,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl)tetrahydrofuran-3-yl)methyl4-methylbenzenesulfonate (IX) (ex APIChem, Catalogue Number: AC-8330, 12.4 g, 27.6 mmol). The reaction mixture was stirred at 30C for 18 hr, cooled to RT and water (200 mL) was added. The resulting mixture was extracted with EtOAc (3 x 200 mL) and the combined organic extracts were washed with brine (2 x 200 mL), and then dried and evaporated in vacuo to afford a brown oil. Analysis of the crude, Boc-protected product (Vila) by 1 H NMR indicated that it contained -10% of the alkene: ( )-1-((2-(2,4- difluorophenyl)-4-methylenetetrahydrofuran-2-yl)methyl)-1 /-/-1 ,2,4-triazole, formed as an elimination by-product. The crude urethane (Vila) was taken up into DCM (150 mL) and treated with TFA (39.0 mL, 502 mmol). After 2 hr at RT the reaction mixture was concentrated in vacuo to remove most of the volatiles and was then diluted with EtOAc (200 mL) and washed with aq. NaOH (2 M, 200 mL). The aq phase was separated and was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with brine (2 x 200 mL) and then dried and evaporated in vacuo to afford a light brown oil. The crude product was purified by flash column chromatography (Si02, 80 g, 0-10% 0.7 M NH3/MeOH in DCM, gradient elution) to afford the title compound, intermediate (V), as a viscous, light brown oil (9.46 g, 80%); R’ 1.91 min (Method b); m/z 470 (M+H)+ (ES+); 1 H NMR delta: 2.07 (3H, s), 2.15 (1 H, dd), 2.36-2.42 (1 H, m), 2.52-2.56 (1 H, m), 2.79-2.81 (4H, m), 2.87-2.90 (4H, m), 3.66 (1 H, dd), 3.73-3.77 (2H, m), 4.04 (1 H, t), 4.57 (2H, dd), 6.64 (1 H, dd), 6.70-6.75 (2H, m), 6.99 (1 H, td), 7.25-7.34 (2H, m), 7.76 (1 H, s) and 8.34 (1 H, s)., 149809-43-8
As the paragraph descriping shows that 149809-43-8 is playing an increasingly important role.
Reference£º
Patent; PULMOCIDE LIMITED; SUNOSE, Mihiro; COLLEY, Thomas Christopher; ITO, Kazuhiro; RAPEPORT, Garth; STRONG, Peter; (55 pag.)WO2016/87878; (2016); A1;,
Tetrahydrofuran – Wikipedia
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