(+/-)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-[[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]-3-nitrobenzoate | 1073117-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-[[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]-3-nitrobenzoate
• 英文别名: 1-cyclohexyloxycarbonyloxyethyl 3-nitro-2-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methylamino]benzoate
• CAS: 1073117-29-9
• 化学式: C₃₀H₃₀N₆O₇
• 分子量: 586.604
• InChiKey: SJTAXDXFRLUDIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+/-)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-[[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]-3-nitrobenzoate 在 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到2-(((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-aminobenzoic acid-1-(((cyclohexyloxy)carbonyl)oxy)ethyl ester
  参考文献：
  名称：

  Novel and Practical Synthesis of Candesartan Cilexetil

  摘要：

  A novel and convergent synthetic route of candesartan cilexetil (API of Atacand), an effective angiotensin II receptor blocker, is described. Cleavage of the N-Boc and N-trityl protective group are implemented simultaneously and formation of the benzimidazole ring is conducted at the last step of this route, which gives candesartan cilexetil in 55% yield over six steps with 99.1% purity (HPLC).

  DOI：

  10.3987/com-10-11944
• 作为产物：
  描述：

  1-(((cyclohexyloxy)carbonyl)oxy)ethyl 2-((tert-butoxycarbonyl)((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate 在 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以39 g的产率得到(+/-)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-[[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]amino]-3-nitrobenzoate
  参考文献：
  名称：

  Novel and Practical Synthesis of Candesartan Cilexetil

  摘要：

  A novel and convergent synthetic route of candesartan cilexetil (API of Atacand), an effective angiotensin II receptor blocker, is described. Cleavage of the N-Boc and N-trityl protective group are implemented simultaneously and formation of the benzimidazole ring is conducted at the last step of this route, which gives candesartan cilexetil in 55% yield over six steps with 99.1% purity (HPLC).

  DOI：

  10.3987/com-10-11944

文献信息

• A NEW PROCESS FOR THE PREPARATION OF CANDESARTAN CILEXETIL
  申请人：Farma GRS, d.o.o.

  公开号：EP3083582B1

  公开（公告）日：2019-06-26
• Novel and Practical Synthesis of Candesartan Cilexetil
  作者：Jingshan Shen、Yongjun Mao、Ruisheng Xiong、Zheng Liu、Haihong Li、Jingkang Shen

  DOI：10.3987/com-10-11944

  日期：——

  A novel and convergent synthetic route of candesartan cilexetil (API of Atacand), an effective angiotensin II receptor blocker, is described. Cleavage of the N-Boc and N-trityl protective group are implemented simultaneously and formation of the benzimidazole ring is conducted at the last step of this route, which gives candesartan cilexetil in 55% yield over six steps with 99.1% purity (HPLC).