2-(4-{4-[4-(3-Cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-benzenesulfonylamino}-phenyl)-N-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-acetamide | 202873-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-{4-[4-(3-Cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-benzenesulfonylamino}-phenyl)-N-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-acetamide
• 英文别名: 2-[4-[[4-[4-(3-cyclopentylpropyl)-5-oxotetrazol-1-yl]phenyl]sulfonylamino]phenyl]-N-[(2R)-2-hydroxy-2-pyridin-3-ylethyl]acetamide
• CAS: 202873-16-3
• 化学式: C₃₀H₃₅N₇O₅S
• 分子量: 605.718
• InChiKey: XFLMYVAVRNOKMV-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(4-{4-[4-(3-Cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-benzenesulfonylamino}-phenyl)-N-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-acetamide 在 dimethyl sulfide borane 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到4-[4-(3-环戊基丙基)-5-羰基-4,5-二氢-1H-四唑-1-基]-N-[4-[2-[2(R)-羟基-2-(3-吡啶基)乙胺基]乙基]苯基]苯磺酰胺
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2
• 作为产物：
  描述：

  4-(氯磺酰)异氰酸苯酯 在 碳酸氢钠 作用下， 以 正辛烷 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 2-(4-{4-[4-(3-Cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-benzenesulfonylamino}-phenyl)-N-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-acetamide
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2