With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.7314-44-5, name is (2,4-Dimethoxyphenyl)methanol, molecular formula is C9H12O3, molecular weight is 168.19, as common compound, the synthetic route is as follows.Recommanded Product: (2,4-Dimethoxyphenyl)methanol
N-(Fmoc)-M1-(Boc)-D-Tryptophan (1 eq., 4.5 g, 8.55 mmol), TBTU (1 eq., 2.74 g, 8.55 mmol) and di-iso-propylethylamine (DIEA, 2 eq., 2.82 mL, 17.1 mmol) were dissolved in DMF (20 mL), stirred at rt for 30 mm under argon atmosphere, treated with an injection of a solutionof 2,4-dimethoxybenzyl alcohol (1.1 eq., 1.58 g, 9.4 mmol, prepared according to Feng, L.; Lv, K.; Liu, M.; Wang, S.; Zhao, J.; You, X.; Li, S.; Cao, J.; Guo, H. Eur. J. Med. Chem. 2012, 55, 125-136) in DMF (5 mL), and stirred at rt for 4h. The reaction mixture was diluted with EtOAc and washed with water (2 x 100 mL) and brine (2 x 100 mL). The organic phases were combined, dried over Na2SO4, filtered and evaporated to a residue that was purified by flashchromatography on silica gel eluting with 20% EtOAc in hexane to afford ester 6 (4.97 g, 7.35 mmol, 86 %) as white solid: mp 67-68 C; Rf 0.29 (20% EtOAc in hexane); 1H NMR (500 MHz, CDCI3) oe 8.11 (brs, 1H), 7.76 (d, J= 7.6 Hz, 2H), 7.58-7.48 (m, 3H), 7.44 (s, 1H), 7.42-7.36 (m, 2H), 7.33 – 7.26 (m, 3H), 7.21 (t, J 7.3 Hz, 1 H), 7.11 (d, J = 8.0 Hz, 1 H), 6.46 – 6.39 (m, 2H), 5.44 (d, J= 8.0 Hz, 1H), 5.12 (s, 2H), 4.78 (dd, J= 13.6, 5.4 Hz, 1H), 4.40-4.28 (m, 2H),4.19 (t, J= 7.3 Hz, 1H), 3.80 (s, 3H), 3.79 (s, 3H), 3.33-3.20 (m, 2H), 1.65 (s, 9H); 13C NMR(125 MHz, CDCI3) 6 171.7, 161.7, 159.2, 155.8, 149.7, 144.0, 143.9, 141.4 (2C), 131.7 (2C),127.8 (2C), 127.2 (2C), 125.3 (2C), 124.6 (2C), 124.5, 124.4, 122.8, 120.1, 119.0, 115.8, 115.4,115.1, 104.2, 98.7, 83.8, 67.3, 63.4, 55.5 (2C), 54.4, 47.3, 28.3 (3C), 28.0; HRMS m/zcalculated for C40H41N208 [M+H] 677.2857; found 677.2859.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,7314-44-5, (2,4-Dimethoxyphenyl)methanol, and friends who are interested can also refer to it.
Reference:
Patent; VALORISATION-RECHERCHE, LIMITED PARTNERSHIP; LUBELL, William D.; ONG, Huy; ZHANG, Jinqiang; MULUMBA, Dilan Mukandila; MARLEAU, Sylvie; OHM, Ragnhild Gaard; AHSANULLAH, -; OMRI, Samy; CHINGLE, Ramesh; (157 pag.)WO2018/79; (2018); A1;,
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