生命科学。
生命科学
合成路线 1(1. 合成:34079-31-7)
产率:49%
合成条件:With pyridine; di- tert -butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane at 20℃;
实验步骤:在1,4-中开始1 - {[(苯基甲基)氧基]羰基} -L-脯氨酸(8.0g,32.09mmol),吡啶(1.5mL),(BoC)2O(9.1g,41.72mmol)的溶液 在室温下加入二恶烷(40mL),加入碳酸氢铵(3.2g,40.43mmol)。 在室温下搅拌过夜后,将反应混合物用EtOAc(100mL)处理,然后将混合物用水(50mL)洗涤,接着用5%H 2 SO 4洗涤。收集有机层,干燥(Na 2 SO 4),过滤。 通过真空蒸发除去挥发物。 将得到的澄清油状物用乙醚研磨。 过滤沉淀物,并在真空下进一步干燥,得到标题化合物,为白色固体(3.9g,49%)。 MH + 249。
参考文献:
- [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 1, p. 84 - 96 [2] Synlett, 2004, # 3, p. 558 - 560 [3] Patent: WO2005/121135, 2005, A1. Location in patent: Page/Page column 240-241 [4] Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95 [5] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631 [6] Tetrahedron Asymmetry, 2004, vol. 15, # 12, p. 1831 - 1834 [7] European Journal of Organic Chemistry, 2005, # 20, p. 4287 - 4295 [8] Synlett, 2006, # 6, p. 889 - 892 [9] Chemische Berichte, 1983, vol. 116, # 5, p. 2037 - 2040 [10] Organic Syntheses, 2008, vol. 85, p. 72 - 87 [11] Carbohydrate Research, 2013, vol. 381, p. 12 - 18 [12] Pharmazie, 1992, vol. 47, # 9, p. 710 - 711 [13] Organic and Biomolecular Chemistry, 2011, vol. 9, # 1, p. 265 - 272 [14] Organic and Biomolecular Chemistry, 2017, vol. 15, # 34, p. 7196 - 7203 [15] Patent: WO2007/67904, 2007, A2. Location in patent: Page/Page column 14; 24 [16] Journal of Pharmaceutical Sciences, 1991, vol. 80, # 9, p. 837 - 842 [17] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 3, p. 591 - 600 [18] Tetrahedron, 1996, vol. 52, # 10, p. 3521 - 3546 [19] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6568 - 6572 [20] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266 [21] Patent: WO2010/111483, 2010, A1. Location in patent: Page/Page column 115-116 [22] Patent: WO2010/138791, 2010, A1. Location in patent: Page/Page column 94-95 [23] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3777 - 3779 [24] Tetrahedron Letters, 2012, vol. 53, # 28, p. 3672 - 3675 [25] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4975 - 4977 [26] Tetrahedron Letters, 2014, vol. 55, # 50, p. 6831 - 6835 [27] Patent: EP2545060, 2015, B1. Location in patent: Paragraph 0313; 0314 [28] Patent: WO2007/77186, 2007, A1