主要作为医药中间体,用于药物合成中的氨基保护或修饰。
医药
合成路线 1(1. 合成:105496-31-9)
产率:93%
合成条件:With triethylamine In tetrahydrofuran at 20℃;
实验步骤:向2000mL圆底烧瓶中加入2-氨基乙-1-醇7a(30g,491mmol)的THF(600mL)溶液,Fmoc-OSu(166g,491mmol)和NEt3( 199克,1.97摩尔)。 将所得溶液在室温下搅拌过夜。 将混合物真空浓缩,并通过硅胶色谱法(乙酸乙酯/石油醚)纯化,得到7b(130g,93%),为白色固体。
参考文献:
- [1] Journal of the American Chemical Society, 2014, vol. 136, # 47, p. 16683 - 16688 [2] Tetrahedron Letters, 2008, vol. 49, # 41, p. 5890 - 5893 [3] Patent: WO2015/51045, 2015, A2. Location in patent: Page/Page column 160 [4] Patent: US2016/215288, 2016, A1. Location in patent: Paragraph 0602; 0607 [5] Tetrahedron, 2007, vol. 63, # 28, p. 6577 - 6586 [6] RSC Advances, 2015, vol. 5, # 78, p. 63407 - 63420 [7] New Journal of Chemistry, 2012, vol. 36, # 8, p. 1556 - 1559 [8] Tetrahedron Letters, 2011, vol. 52, # 22, p. 2808 - 2811
合成路线 2(2. 合成:105496-31-9)
产率:87%
合成条件:at 20℃; for 0.03 h; Sonication; Irradiation; Green chemistry
实验步骤:通用方法:将胺(1mmol)和Fmoc-Cl(1.1mmol)在纯净条件下置于玻璃管中并超声处理合适的时间(如表1,2和3中所示)。 所有反应均在室温水浴中进行。 在反应完成后(如TLC所示),向混合物中加入5cm 3乙醚。 N-Fmoc衍生物结晶并以良好至极好的产率获得。 通过从乙醚中重结晶完成产物的纯化。
参考文献:
- [1] Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 255 - 273 [2] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 871 - 882 [3] Journal of Carbohydrate Chemistry, 2012, vol. 31, # 4-6, p. 384 - 419 [4] Russian Journal of Bioorganic Chemistry, 2005, vol. 31, # 4, p. 352 - 356 [5] European Journal of Organic Chemistry, 2008, # 34, p. 5786 - 5797 [6] Green Chemistry, 2011, vol. 13, # 12, p. 3355 - 3359 [7] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 3, p. 546 - 550 [8] Chemical Communications, 2014, vol. 50, # 54, p. 7132 - 7135 [9] Patent: WO2018/149419, 2018, A1. Location in patent: Paragraph 001283 [10] Tetrahedron Letters, 1993, vol. 34, # 39, p. 6189 - 6192 [11] Tetrahedron Letters, 2002, vol. 43, # 17, p. 3125 - 3128 [12] Patent: US2006/51291, 2006, A1. Location in patent: Page/Page column 7; 24 [13] Patent: US5599587, 1997, A [14] Patent: WO2006/39668, 2006, A2. Location in patent: Page/Page column 40 [15] Patent: WO2006/105123, 2006, A2. Location in patent: Page/Page column 50