With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.
951127-25-6, Compound 3(200 mg, 0.611 mmol) and HSCH2CH2SH (0.11 mL, 1.53 mmol) were dissolved in DCM (10 mL) and treated with BF3 etherate (0.077 mL, 0.611 mmol) at RT. The resulting solution was stirred at RT for 1 h, and quenched with sat. aq. NaHCO3 solution. The organic phase was separated andextracted with DCM for several times. Combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 60 – 90 oC PE:EtOAc =10:1) to yield the product 8 (white solid, 212 mg, 0.525 mmol, 86%). M.p. 156.6 – 159.0 (dichloromethane); Rf 0.2 (10 : 1, petroleum ether : EtOAc); [alpha]D -7.88 (c 0.165, CHCl3) ; HPLC tR 3.6min; 1H NMR (600 MHz, CDCl3) delta 7.28 (s, 1H, ArH), 6.95 (s, 2H, ArH), 4.45 (d, J = 9.0 Hz, 1H, NHBoc),4.42 (d, J = 9.9 Hz, 1H, H-1), 4.00 (dd, J = 12.0 Hz, 1.8 Hz, 1H, H-5), 3.86 (d, J = 9.0 Hz, 1H, H-2), 3.74(d, J = 11.6 Hz, 1H, H-5?), 3.34 (ddd, J = 22.8, 12.0, 5.8 Hz, 4H, Dithiolane-CH2), 2.63 (d, J = 12.9 Hz, 1H,H-3), 2.19 – 2.01 (m, 1H, H-3?), 1.27 (s, 9H, C(CH3)3); 13C NMR (151 MHz, CDCl3) delta 159.10 (d, J C-F =243.0 Hz, ArC), 156.29 (d, J C-F = 240.6 Hz, ArC), 154.55 (C=O), 128.00 (dd, J C-C-F = 15.5, 7.9 Hz, ArC),116.40 – 116.13 (m, ArC), 116.13 – 115.81 (m, ArC), 115.34 – 115.07 (m, ArC), 79.75 (C(CH3)3), 77.84(C-5), 76.01 (C-1), 64.88 (C-4), 52.80 (C-2), 46.52 (C-3), 38.96 (Dithiolane-CH2), 38.78(Dithiolane-CH2), 28.24 (C(CH3)3); HRMS (ESI+) calcd. For C18H23F2NNaO3S2+426.0980, found426.0968.
The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Li, You; Liu, Tongchao; Li, Chungang; Xiong, Bing; Zhao, Dongmei; Cheng, Maosheng; Chen, Guohua; Shen, Jingkang; Chen, Yue-Lei; Synthetic Communications; vol. 47; 4; (2017); p. 357 – 363;,
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