89711-08-0 N-叔丁氧羰基-2-氨基乙醛

合成路线 2（2. 合成：89711-08-0）

产率：69% 合成条件：With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; Inert atmosphere 实验步骤：在氩气氛下向圆底烧瓶中加入48（0.80g，10.0mmol）和IBX36（2.80g，10.0mmol）。 将DMSO（25mL）加入到混合物中，然后在室温下继续搅拌过夜。 将反应混合物用水（200mL）淬灭并减压过滤。 滤液用乙酸乙酯萃取。 将有机层干燥（Na 2 SO 4）并减压浓缩。 通过SiO 2柱色谱法（CHCl 3：EtOAc = 7：3）纯化粗残余物，得到49（69％;点亮55％37），为油状物; 1H NMR（500MHz，CDCl3）：d 9.65（2H，br s，HCO），5.16（1H，br，NH），4.06（2H，s，CH2），1.45（9H，s，C（CH3）3）。 参考文献：

• [1] Synthesis, 2011, # 14, p. 2321 - 2333 [2] Chemical Communications, 2007, # 21, p. 2136 - 2138 [3] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10036 - 10039 [4] Helvetica Chimica Acta, 1997, vol. 80, # 4, p. 1244 - 1259 [5] Organic and Biomolecular Chemistry, 2003, vol. 1, # 20, p. 3527 - 3534 [6] Phytochemistry (Elsevier), 1990, vol. 29, # 3, p. 701 - 703 [7] European Journal of Organic Chemistry, 2014, vol. 2014, # 24, p. 5331 - 5345 [8] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4905 - 4908 [9] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1094 - 1112 [10] Patent: WO2010/24451, 2010, A1. Location in patent: Page/Page column 50; 51 [11] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 1, p. 275 - 278 [12] Journal of Organic Chemistry, 2002, vol. 67, # 12, p. 4017 - 4029 [13] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 2, p. 239 - 252 [14] Patent: US2012/264727, 2012, A1. Location in patent: Page/Page column 33; 34 [15] Patent: EP2706062, 2014, A2. Location in patent: Paragraph 0069 [16] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2487 - 2493 [17] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 2891 - 2893 [18] Heterocycles, 2003, vol. 60, # 4, p. 791 - 798 [19] Synthesis, 2003, # 18, p. 2805 - 2810 [20] Synlett, 2003, # 10, p. 1539 - 1541 [21] Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 1963 - 1977 [22] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1486 - 1490 [23] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3295 - 3298 [24] Patent: US5206235, 1993, A [25] Patent: US5438136, 1995, A [26] Patent: WO2005/41888, 2005, A2. Location in patent: Page/Page column 86 [27] Patent: US7544794, 2009, B1. Location in patent: Page/Page column 14-15 [28] Patent: WO2004/55008, 2004, A1. Location in patent: Page 49 [29] Patent: WO2012/82436, 2012, A2. Location in patent: Page/Page column 288 [30] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3140 - 3144 [31] Patent: WO2015/88565, 2015, A1. Location in patent: Paragraph 00225 [32] RSC Advances, 2016, vol. 6, # 31, p. 25713 - 25723 [33] Patent: JP2016/190813, 2016, A. Location in patent: Paragraph 0066-0068 [34] Patent: CN108129404, 2018, A. Location in patent: Paragraph 0106; 0107 [35] Patent: WO2005/41888, 2005, A2. Location in patent: Page/Page column 86

合成路线 3（3. 合成：89711-08-0）

产率：56% 合成条件：With sodium periodate In water at 20℃; for 2 h; 实验步骤：步骤2 2-氧代乙基氨基甲酸叔丁酯：将高碘酸钠（41.52g; 194mmol; 1.00当量）分批加入到溶解在水中的2,3-二羟基丙基氨基甲酸叔丁酯（37g; 194mmol; 1.00当量）中（300毫升）。 将所得溶液在环境温度下搅拌约2小时。 过滤除去固体。 用二氯甲烷标准萃取后处理，得到标题产物，为白色固体（17g;产率56％）。 1 H NMR（300MHz，CDCl 3）δ9.65（s，1H），5.26（s，1H），4.07（d，J = 4.5Hz，2H），1.46（s，9H）。 参考文献：

• [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 2, p. 445 - 451 [2] Journal of the American Chemical Society, 2015, vol. 137, # 39, p. 12442 - 12445 [3] Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3339 - 3345 [4] Patent: US2010/9950, 2010, A1. Location in patent: Page/Page column 24 [5] Patent: US6750348, 2004, B1. Location in patent: Page column 66 [6] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4969 - 4974 [7] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4509 - 4512 [8] Patent: WO2018/175927, 2018, A2. Location in patent: Paragraph 00303