methyl (R)-2(4-chlorobenzenesulfonyloxyl)-2-(2-chlorophenyl)acetate | 223123-65-7

• 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: methyl (R)-2(4-chlorobenzenesulfonyloxyl)-2-(2-chlorophenyl)acetate
• 英文别名: methyl (2R)-2-(2-chlorophenyl)-2-(4-chlorophenyl)sulfonyloxyacetate
• CAS: 223123-65-7
• 化学式: C₁₅H₁₂Cl₂O₅S
• 分子量: 375.229
• InChiKey: CIBFZAMKUSNKFH-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-2(4-chlorobenzenesulfonyloxyl)-2-(2-chlorophenyl)acetate 、 在 potassium hydrogencarbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 methyl (2S,3Z)-2-(2-chlorophenyl)-2-[3-(2-methoxy-2-oxoethylidene)-4-((2-(3-methoxyphenyl)-2-oxoethyl)sulfanyl)piperidin-1-yl]acetate 、 methyl (2S,3Z)-2-(2-chlorophenyl)-2-[3-(2-methoxy-2-oxoethylidene)-4-((2-(3-methoxyphenyl)-2-oxoethyl)sulfanyl)piperidin-1-yl]acetate
  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

• US6894186B2
  申请人：——

  公开号：US6894186B2

  公开（公告）日：2005-05-17
• 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.