4-乙基磺酰基苯基乙酸主要作为医药中间体,用于相关药物的合成制备。
医药
合成路线 1(1. 合成:383135-47-5)
产率:91%
合成条件:With water; sodium hydroxide In ethanol at 20℃; for 12 h;
实验步骤:向50mL圆底烧瓶中加入2-(4-(乙基磺酰基)苯基)乙酸乙酯(2.5g,0.0098mol)和乙醇(18mL)。 向同一烧瓶中加入氢氧化钠水溶液(1.42g,0.0355mol,在18mL水中)。 将反应混合物在室温下搅拌12小时。 减压蒸发挥发物,得到残余物。 将残余物用1N HCl酸化至pH 5.0并用乙酸乙酯萃取。 分离有机层,用盐水洗涤并经硫酸钠干燥。 减压蒸发溶剂,得到标题化合物[2.4g,91%]。 1 H NMR(400MHz,DMSO-i):δ12.5(brs,1H),7.84(d,= 8.4Hz,2H),7.56(d,= 8.4Hz,2H),3.74(s,2H),3.13( q,T = 7.2Hz,J'= 14.8Hz,2H),1.20(t,= 7.6Hz,3H)。
参考文献:
- [1] Patent: WO2014/125426, 2014, A1. Location in patent: Page/Page column 32 [2] Patent: WO2015/83130, 2015, A1. Location in patent: Page/Page column 50-51 [3] Patent: WO2015/101928, 2015, A1. Location in patent: Page/Page column 33; 35 [4] Patent: WO2016/185342, 2016, A1. Location in patent: Page/Page column 36 [5] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7796 - 7813 [6] Patent: WO2015/116904, 2015, A1. Location in patent: Paragraph 00118; 0123 [7] Patent: WO2012/28100, 2012, A1. Location in patent: Page/Page column 14 [8] Patent: WO2012/27965, 2012, A1. Location in patent: Page/Page column 15 [9] Patent: WO2012/100734, 2012, A1. Location in patent: Page/Page column 13 [10] Patent: WO2012/100732, 2012, A1. Location in patent: Page/Page column 12-13 [11] Patent: WO2014/179564, 2014, A1. Location in patent: Paragraph 00121; 00126 [12] Patent: WO2015/159233, 2015, A1. Location in patent: Page/Page column 125
合成路线 2(2. 合成:383135-47-5)
产率:10 g
合成条件:With vanadium pentoxide; dihydrogen peroxide In acetonitrile at 0 - 30℃; for 2 h;
实验步骤:在0℃下向搅拌的步骤3的产物(12g,61.1mmol)和五氧化二钒(100mg)的CH 3 CN(50ml)溶液中加入50%过氧化氢(15ml)并在室温下搅拌2小时。 将反应混合物缓慢倒入冰冷的水中,得到的产物用EtOAc萃取。 蒸馏出有机层,得到10g标题产物,为固体。 1 H NMR(DMSO-d6):12.54(bs,1H),7.83(d,/ = 8.0Hz,2H),7.55(d,/ = 8.4Hz,2H),3.73(s,2H),3.30(q, / = 7.2Hz,2H),1.09(t,J = 7.2Hz,3H)。
参考文献:
- [1] Patent: WO2018/11746, 2018, A1. Location in patent: Page/Page column 40