methanesulfonic acid 3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propyl ester | 1030603-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methanesulfonic acid 3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propyl ester
• 英文别名: 3-[(1S)-5-Chloro-1-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-yl]propyl methanesulfonate；3-[(1S)-5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl methanesulfonate
• CAS: 1030603-35-0
• 化学式: C₁₉H₂₀Cl₂O₃S
• 分子量: 399.338
• InChiKey: LUBMGKHSJBUGJK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propyl ester 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 111.0h， 生成 (2S)-2-{3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propylamino}propionic acid
  参考文献：
  名称：

  Route Scouting and Process Development of Lu AA26778

  摘要：

  Route scouting and process development for the synthesis of (S)-2-({3-[(S)-5-chloro-1-(4-chloro-phenyl)indan-1-yl]propyl}methyl- amino)propionic acid, Lu AA26778, are described. The strategy is based on a short synthesis and SMB resolution of a key chiral intermediate for the introduction of one of the two stereocenters. The second stereocenter is introduced via a commercially available alanine ester, optionally bearing a N-methyl group. The main concern during scale-up of the synthesis was the safety of a step incorporating sodium dimsylate (the sodium salt of DMSO): this problem was solved using THF as a safety blanket in the large-scale process.

  DOI：

  10.1021/op7002584
• 作为产物：
  描述：

  5-氯-1-茚酮 在 盐酸 、 pseudomonas fluorescens lipase 、 5%-palladium/activated carbon 、 氢气 、 碘 、 sodium hydride 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 、 mineral oil 为溶剂， 65.0 ℃ 、300.01 kPa 条件下， 反应 92.5h， 生成 methanesulfonic acid 3-[(S)-5-chloro-1-(4-chlorophenyl)indan-1-yl]propyl ester
  参考文献：
  名称：

  Route Scouting and Process Development of Lu AA26778

  摘要：

  Route scouting and process development for the synthesis of (S)-2-({3-[(S)-5-chloro-1-(4-chloro-phenyl)indan-1-yl]propyl}methyl- amino)propionic acid, Lu AA26778, are described. The strategy is based on a short synthesis and SMB resolution of a key chiral intermediate for the introduction of one of the two stereocenters. The second stereocenter is introduced via a commercially available alanine ester, optionally bearing a N-methyl group. The main concern during scale-up of the synthesis was the safety of a step incorporating sodium dimsylate (the sodium salt of DMSO): this problem was solved using THF as a safety blanket in the large-scale process.

  DOI：

  10.1021/op7002584

文献信息

• Route Scouting and Process Development of Lu AA26778
  作者：Allan C. Dahl、Michael J. Mealy、Martin A. Nielsen、Lars O. Lyngsø、Cristina Suteu

  DOI：10.1021/op7002584

  日期：2008.5.1

  Route scouting and process development for the synthesis of (S)-2-(3-[(S)-5-chloro-1-(4-chloro-phenyl)indan-1-yl]propyl}methyl- amino)propionic acid, Lu AA26778, are described. The strategy is based on a short synthesis and SMB resolution of a key chiral intermediate for the introduction of one of the two stereocenters. The second stereocenter is introduced via a commercially available alanine ester, optionally bearing a N-methyl group. The main concern during scale-up of the synthesis was the safety of a step incorporating sodium dimsylate (the sodium salt of DMSO): this problem was solved using THF as a safety blanket in the large-scale process.