化学合成。
化学合成
合成路线 1(2. 合成:156939-62-7)
产率:94%
合成条件:With pyridine-SO 3 complex; N-ethyl-N,N-diisopropylamine In dichloromethane; dimethyl sulfoxide at -40℃; for 1.25 h;
实验步骤:向N-(9-芴基甲氧基羰基)乙醇(5.0g,18mmol)的二氯甲烷(50mL)悬浮液中加入二异丙基乙胺(12.4mL,70.6mmol)。 将反应混合物冷却至-40℃,并在15分钟内加入三氧化硫吡啶络合物(11.2g,70.6mmol)的二甲基亚砜(49.5mL)溶液。 在-40℃下搅拌1小时后,将反应混合物用冰水和盐水的混合物处理。 除去溶剂,过滤得到的灰白色沉淀,真空干燥。 通过硅胶快速色谱法纯化,用乙酸乙酯/己烷(1/1)洗脱,得到N-Fmoc甘氨酸21-a(4.7g,94%)。
参考文献:
- [1] Organic Letters, 2002, vol. 4, # 17, p. 3001 - 3003 [2] Synthetic Communications, 2007, vol. 37, # 20, p. 3493 - 3499 [3] Patent: WO2018/149419, 2018, A1. Location in patent: Paragraph 001283; 001284 [4] European Journal of Organic Chemistry, 2008, # 34, p. 5786 - 5797 [5] Patent: WO2006/66183, 2006, A2. Location in patent: Page/Page column 63 [6] Patent: WO2005/118584, 2005, A2. Location in patent: Page/Page column 57 [7] Patent: US2010/145036, 2010, A1. Location in patent: Page/Page column 87 [8] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 871 - 882 [9] Tetrahedron Letters, 2002, vol. 43, # 17, p. 3125 - 3128 [10] Journal of the American Chemical Society, 2003, vol. 125, # 21, p. 6517 - 6531 [11] Tetrahedron, 2007, vol. 63, # 28, p. 6577 - 6586 [12] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 6126 - 6141