化学合成;生命科学。
化学合成;生命科学
合成路线 1(1. 合成:115962-35-1)
产率:100%
合成条件:With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144 h;
实验步骤:将(S)-1,2,3,4-四氢异喹啉-3-羧酸(50.0g,282mmol)在1,4-二恶烷(1000mL)和水(500mL)的混合物中剧烈搅拌。 加入碳酸氢钠(47.4g,564mmol)和Boc酐(67.7g,310mmol),将反应混合物在室温剧烈搅拌6天。 将混合物真空浓缩,将残余物溶于水(2000mL)中。 加入30%w / v的硫酸氢钠一水合物水溶液(300mL),用氯仿(3×1000mL)萃取混合物。 将合并的有机萃取液用盐水洗涤,用硫酸钠干燥并真空浓缩,得到所需化合物(90.0g,定量),为稠浆状物。 LCMS-B:RT 3.64分钟; m / z 178.1 [M-Boc + 2H] +; m / z 276.1 [M-H] -
参考文献:
- [1] Patent: WO2017/153513, 2017, A1. Location in patent: Page/Page column 78 [2] Patent: WO2017/153515, 2017, A1. Location in patent: Page/Page column 62 [3] Patent: WO2017/153520, 2017, A1. Location in patent: Page/Page column 44; 47 [4] Patent: WO2017/153519, 2017, A1. Location in patent: Page/Page column 56; 59 [5] Tetrahedron Letters, 2001, vol. 42, # 43, p. 7559 - 7561 [6] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4828 - 4832 [7] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4833 - 4837 [8] Tetrahedron Letters, 2004, vol. 45, # 38, p. 7081 - 7085 [9] Organic Letters, 2016, vol. 18, # 19, p. 5070 - 5073 [10] Patent: WO2011/61318, 2011, A1. Location in patent: Page/Page column 22 [11] Patent: WO2016/34673, 2016, A1. Location in patent: Page/Page column 71; 74 [12] Journal of Materials Chemistry B, 2017, vol. 5, # 5, p. 917 - 927 [13] International Journal of Nanomedicine, 2018, vol. 13, p. 1139 - 1158 [14] Organic Letters, 2017, vol. 19, # 21, p. 5826 - 5829 [15] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 1719 - 1729 [16] European Journal of Organic Chemistry, 2002, # 23, p. 3936 - 3943 [17] European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4904 - 4919 [18] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 2, p. 871 - 882 [19] Tetrahedron, 2014, vol. 70, # 23, p. 3707 - 3713 [20] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 24, p. 3623 - 3631 [21] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 20, p. 2883 - 2889 [22] Tetrahedron Asymmetry, 2010, vol. 21, # 9-10, p. 1238 - 1245 [23] Chinese Chemical Letters, 2012, vol. 23, # 3, p. 297 - 300 [24] Chemistry - A European Journal, 2015, vol. 21, # 51, p. 18589 - 18593 [25] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965