2-fluoro-2-(4-iodo-phenyl)-propylamine (S)-(-)-(2)-pyrrolidone-5-carboxylic acid salt

• 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-fluoro-2-(4-iodo-phenyl)-propylamine (S)-(-)-(2)-pyrrolidone-5-carboxylic acid salt
• 化学式: C₅H₇NO₃*C₉H₁₁FIN
• 分子量: 408.211
• InChiKey: CLJVQOXAMRJYDI-BFFRJAOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.42
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-fluoro-2-(4-iodo-phenyl)-propylamine (S)-(-)-(2)-pyrrolidone-5-carboxylic acid salt 在 potassium carbonate 、 钯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲基叔丁基醚 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.43h， 生成 (S)-4'-[1-fluoro-1-methyl-2-(propane-2-sulfonylamino)-ethyl]-biphenyl-4-carboxylic acid methylamide
  参考文献：
  名称：

  Diastereomeric Salt Resolution Based Synthesis of LY503430, an AMPA (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid) Potentiator

  摘要：

  This article describes the development and optimization of chemical reactions and subsequent preparation of the API LY503430 under cGMPs to fund first human dose (FHD) clinical evaluation as a potential therapeutic agent for Parkinson's disease. Reasons and rationale are presented for changes in solvents and reagents. One of the major developments presented here is the replacement of a chiral chromatography with a diastereomeric salt resolution. This article also discusses a preferred orientation issue with LY503430 which complicated the XRPD analysis.

  DOI：

  10.1021/op0500741
• 作为产物：
  描述：

  1-碘-4-丙-1-烯-2-基苯 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 triethylamine tris(hydrogen fluoride) 作用下， 以 丙醇 、 乙醇 、 正庚烷 、 二氯甲烷 、 甲基叔丁基醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 2-fluoro-2-(4-iodo-phenyl)-propylamine (S)-(-)-(2)-pyrrolidone-5-carboxylic acid salt
  参考文献：
  名称：

  Diastereomeric Salt Resolution Based Synthesis of LY503430, an AMPA (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid) Potentiator

  摘要：

  This article describes the development and optimization of chemical reactions and subsequent preparation of the API LY503430 under cGMPs to fund first human dose (FHD) clinical evaluation as a potential therapeutic agent for Parkinson's disease. Reasons and rationale are presented for changes in solvents and reagents. One of the major developments presented here is the replacement of a chiral chromatography with a diastereomeric salt resolution. This article also discusses a preferred orientation issue with LY503430 which complicated the XRPD analysis.

  DOI：

  10.1021/op0500741

文献信息

• Diastereomeric Salt Resolution Based Synthesis of LY503430, an AMPA (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid) Potentiator
  作者：Nicholas A. Magnus、James A. Aikins、Jason S. Cronin、William D. Diseroad、Amy D. Hargis、Michael E. LeTourneau、Bruce E. Parker、Susan M. Reutzel-Edens、John P. Schafer、Michael A. Staszak、Gregory A. Stephenson、Shella L. Tameze、Lisa M. H. Zollars

  DOI：10.1021/op0500741

  日期：2005.9.1

  This article describes the development and optimization of chemical reactions and subsequent preparation of the API LY503430 under cGMPs to fund first human dose (FHD) clinical evaluation as a potential therapeutic agent for Parkinson's disease. Reasons and rationale are presented for changes in solvents and reagents. One of the major developments presented here is the replacement of a chiral chromatography with a diastereomeric salt resolution. This article also discusses a preferred orientation issue with LY503430 which complicated the XRPD analysis.