2-(((3Z,4R)-1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4-(2-(3-methoxyphenyl)-2-oxoethyl)sulfanyl)piperidin-3-ylidene)acetic acid | 1430373-14-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(((3Z,4R)-1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4-(2-(3-methoxyphenyl)-2-oxoethyl)sulfanyl)piperidin-3-ylidene)acetic acid
• 英文别名: (Z)-2-((R)-1-((S)-1-(2-Chlorophenyl)-2-methoxy-2-oxoethyl)-4-((2-(3-methoxyphenyl)-2-oxoethyl)thio)piperidin-3-ylidene)acetic acid；(2Z)-2-[(4R)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-[2-(3-methoxyphenyl)-2-oxoethyl]sulfanylpiperidin-3-ylidene]acetic acid
• CAS: 1430373-14-0
• 化学式: C₂₅H₂₆ClNO₆S
• 分子量: 504.004
• InChiKey: FNCOEMFSIDGTAR-AOAWOYPYSA-N

物化性质

• 熔点：
  >36°C (dec.)
• 沸点：
  669.7±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、二氯甲烷（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 盐酸 、 草酰氯 、 sodium hydride 、 碳酸氢钠 、 potassium hydrogencarbonate 、 二甲基亚砜 、 间氯过氧苯甲酸 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 、 mineral oil 为溶剂， 反应 176.75h， 生成 2-(((3Z,4R)-1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4-(2-(3-methoxyphenyl)-2-oxoethyl)sulfanyl)piperidin-3-ylidene)acetic acid
  参考文献：
  名称：

  Synthesis of the stabilized active metabolite of clopidogrel

  摘要：

  The convergent synthesis of the stabilized active metabolite of clopidogrel was achieved in eleven steps from commercially available 1,2,3,6-tetrahydropyridine and 2-bromo-3'-methoxy acetophenone (MPBr). This synthetic route used a standard Horner-Wadsworth-Emmons reaction allowing the introduction of a Z exocyclic double bond. A selective hydrolysis of an acrylic methyl ester moiety, isolated by an efficient and reliable preparative chiral chromatography at gram scale, released the title compound with a 98% LC purity and d.e. >99%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.037

文献信息

• Chemical Synthesis of Clopidogrel Active Metabolites and Disulfide Conjugate Prodrugs
  申请人：Board of Regents, The University of Texas System

  公开号：US20210093624A1

  公开（公告）日：2021-04-01

  A method of synthesizing a clopidogrel metabolite is provided. A piperidone intermediate is formed from a mandelate. An asymmetric ketone reduction of the piperidone intermediate is performed. A mercapto installation is performed on the piperidone intermediate to form a clopidogrel metabolite that includes a 4-carbon chiral center having an (R) configuration.

  提供一种合成氯吡格雷代谢物的方法。从曼德酸形成哌啶酮中间体。对哌啶酮中间体进行不对称酮还原。在哌啶酮中间体上进行巯基安装，形成包括一个4碳手性中心，具有(R)构型的氯吡格雷代谢物。
• Synthesis of the stabilized active metabolite of clopidogrel
  作者：Guillaume Bluet、Jorg Blankenstein、Eric Brohan、Céline Prévost、Michel Chevé、Joseph Schofield、Sébastien Roy

  DOI：10.1016/j.tet.2014.04.037

  日期：2014.6

  The convergent synthesis of the stabilized active metabolite of clopidogrel was achieved in eleven steps from commercially available 1,2,3,6-tetrahydropyridine and 2-bromo-3'-methoxy acetophenone (MPBr). This synthetic route used a standard Horner-Wadsworth-Emmons reaction allowing the introduction of a Z exocyclic double bond. A selective hydrolysis of an acrylic methyl ester moiety, isolated by an efficient and reliable preparative chiral chromatography at gram scale, released the title compound with a 98% LC purity and d.e. >99%. (C) 2014 Elsevier Ltd. All rights reserved.