methyl trans-4-{2-[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)benzoyl]hydrazine-1-carbonyl}cyclohexane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl trans-4-{2-[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)benzoyl]hydrazine-1-carbonyl}cyclohexane-1-carboxylate
• 英文别名: Methyl 4-[[[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)benzoyl]amino]carbamoyl]cyclohexane-1-carboxylate
• 化学式: C₂₈H₄₁N₃O₅
• 分子量: 499.651
• InChiKey: ALQBAFHSNXWQNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl trans-4-{2-[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)benzoyl]hydrazine-1-carbonyl}cyclohexane-1-carboxylate 在 tetraphosphorus decasulfide 、 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 trans-4-{5-[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)-phenyl]-1,3,4-thiadiazol-2-yl}cyclohexylmethanol
  参考文献：
  名称：

  Development of a Practical and Scalable Synthesis of the Side Chain for ASP9726, a Successor of Micafungin

  摘要：

  Here, we describe a practical and scalable synthesis of!, which is a useful side chain of ASP9726 (2), a successor of Micafungin. For large-scale synthesis of 1, reaction conditions were optimized to control impurities and increase yield. In particular, we utilized a high-yield thiadiazole ring formation to prepare thiadiazole 12, a step which was improved by optimization of reaction conditions and isolation method. Further, the number of steps was reduced from 10 to 9, and hazardous reactions were also avoided. Consequently, this process was scaled to produce 21.7 kg of 1 with overall yield improvement from 36.7% to 56.6%.

  DOI：

  10.1021/op400211t
• 作为产物：
  描述：

  对氟苯甲酸乙酯 在 potassium carbonate 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 methyl trans-4-{2-[4-(4-cyclohexyl-4-methoxypiperidin-1-yl)benzoyl]hydrazine-1-carbonyl}cyclohexane-1-carboxylate
  参考文献：
  名称：

  Development of a Practical and Scalable Synthesis of the Side Chain for ASP9726, a Successor of Micafungin

  摘要：

  Here, we describe a practical and scalable synthesis of!, which is a useful side chain of ASP9726 (2), a successor of Micafungin. For large-scale synthesis of 1, reaction conditions were optimized to control impurities and increase yield. In particular, we utilized a high-yield thiadiazole ring formation to prepare thiadiazole 12, a step which was improved by optimization of reaction conditions and isolation method. Further, the number of steps was reduced from 10 to 9, and hazardous reactions were also avoided. Consequently, this process was scaled to produce 21.7 kg of 1 with overall yield improvement from 36.7% to 56.6%.

  DOI：

  10.1021/op400211t

文献信息

• Development of a Practical and Scalable Synthesis of the Side Chain for ASP9726, a Successor of Micafungin
  作者：Shinya Yoshida、Atsushi Ohigashi、Yasuhiro Morinaga、Norio Hashimoto、Takumi Takahashi、Shigeru Ieda、Minoru Okada

  DOI：10.1021/op400211t

  日期：2013.10.18

  Here, we describe a practical and scalable synthesis of!, which is a useful side chain of ASP9726 (2), a successor of Micafungin. For large-scale synthesis of 1, reaction conditions were optimized to control impurities and increase yield. In particular, we utilized a high-yield thiadiazole ring formation to prepare thiadiazole 12, a step which was improved by optimization of reaction conditions and isolation method. Further, the number of steps was reduced from 10 to 9, and hazardous reactions were also avoided. Consequently, this process was scaled to produce 21.7 kg of 1 with overall yield improvement from 36.7% to 56.6%.