(S)-2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol

• 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: (S)-2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol
• 英文别名: (S)-albuterol sulfate；S-salbutamol sulfate；4-[(1S)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol; sulfuric acid；4-[(1S)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol;sulfuric acid
• 化学式: 2C₁₃H₂₁NO₃*H₂O₄S
• 分子量: 576.709
• InChiKey: OVICLFZZVQVVFT-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  硫酸沙丁胺醇 以 甲醇 为溶剂， 生成 R-沙丁胺醇盐酸盐 、 (S)-2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol
  参考文献：
  名称：

  Enantiomeric resolution of albuterol sulfate by preferential crystallization

  摘要：

  Albuterol is a beta(2)-adrenoceptor agonist prescribed for the treatment of bronchial asthma; it exists as a racemate and its bronchodilator activity resides in the (R)-isomer or levalbuterol. The aim of this study was to determine a methodology that would separate the enantiomers of albuterol by preferential crystallization after a conglomerate is identified within its derivatives. We found that albuterol sulfate behaves as a conglomerate showing the characteristic alpha(x)-value = 2 (mole fraction solubility ratio of racemate vs enantiomer), the V-shaped ternary phase diagram and the preferential crystallization by seeding with the pure enantiomer. On the basis of these characteristics, we separated the enantiomers by entrainment, and crystallizing out a saturated methanolic solution of albuterol sulfate at 15 degrees C. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.010

文献信息

• Predictability of Enantiomeric Chromatographic Behavior on Various Chiral Stationary Phases Using Typical Reversed Phase Modeling Software
  作者：Hebatallah A. Wagdy、Rasha S. Hanafi、Rasha M. El-Nashar、Hassan Y. Aboul-Enein

  DOI：10.1002/chir.22154

  日期：2013.9

  apply chiral chromatographic separation techniques in their mass production strategy rather than asymmetric synthesis. The present work aims to investigate the predictability of chromatographic behavior of enantiomers using DryLab HPLC method development software, which is typically used to predict the effect of changing various chromatographic parameters on resolution in the reversed phase mode. Three

  世界各地的制药公司倾向于将手性色谱分离技术应用于其批量生产策略，而不是不对称合成。本工作旨在研究使用DryLab HPLC方法开发软件对映异构体色谱行为的可预测性，该软件通常用于预测在反相模式下改变各种色谱参数对分离度的影响。测试了三种不同类型的手性固定相的可预测性：基于大环抗生素的色谱柱（Chirobiotic V和T），基于多糖的手性色谱柱（Chiralpak AD-RH）和基于蛋白质的手性色谱柱（Ultron ES-OVM）。进行了初步的基本运行，然后在完成峰跟踪后导出到DryLab。对于几种探针在Chirobiotic V上的分离，有可能预测％有机流动相对分离的影响：外消旋普萘洛尔的准确度为97.80％；普萘洛尔和硫酸特布他林的外消旋物的混合物，以及普萘洛尔和沙丁胺醇硫酸盐的外消旋物，有机流动相百分比的影响平均准确度为90.46％，pH值影响的平均准确度为98.39％；和外消旋华法林对有机流动相的影响准确度为93