[3(2S),4R]-3-[2-ethyl-3-[4-methoxy-3-(benzyloxycarbonyl)phenyl]propionyl]-4-benzyloxazolidin-2-one | 311771-69-4

• 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: [3(2S),4R]-3-[2-ethyl-3-[4-methoxy-3-(benzyloxycarbonyl)phenyl]propionyl]-4-benzyloxazolidin-2-one
• 英文别名: [3(2S),4R]-3-[2-ethyl-3-(4-methoxy-3-(benzyloxycarbonyl)phenyl)propionyl]-4-benzyl-2-oxazolidinone；benzyl 5-[3-[4-(R)-benzyl-2-oxo-1,3-oxazolidine-3-yl]-2-(S)-ethyl-3-oxopropyl]-2-methoxybenzoate；benzyl 5-[(2S)-2-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]butyl]-2-methoxybenzoate
• CAS: 311771-69-4
• 化学式: C₃₀H₃₁NO₆
• 分子量: 501.579
• InChiKey: IBDDVKDAGLQTQJ-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3(2S),4R]-3-[2-ethyl-3-[4-methoxy-3-(benzyloxycarbonyl)phenyl]propionyl]-4-benzyloxazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到[5(2S,4R)]-2-methoxy-5-[[2-(2-oxo-4-benzyloxazolidin-3-yl)carbonyl]pentyl]benzoic acid
  参考文献：
  名称：

  有效的不对称合成（S）-2-乙基苯基丙酸衍生物，人过氧化物酶体增殖物激活受体α的选择性激动剂。

  摘要：

  通过使用Evans手性恶唑烷酮技术作为关键步骤，可以高光学纯度有效地制备光学活性的苯基丙酸衍生物，它是人过氧化物酶体增殖物激活的受体α的选择性激动剂。

  DOI：

  10.1016/s0960-894x(02)00375-x
• 作为产物：
  描述：

  5-甲酰基-2-甲氧基苯甲酸 在 sodium tetrahydroborate 、 sodium hexamethyldisilazane 、 三溴化磷 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 [3(2S),4R]-3-[2-ethyl-3-[4-methoxy-3-(benzyloxycarbonyl)phenyl]propionyl]-4-benzyloxazolidin-2-one
  参考文献：
  名称：

  SUBSTITUTED PHENYLPROPIONIC ACID DERIVATIVES AS AGONISTS TO HUMAN PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR ALPHA(PPAR)

  摘要：

  公开号：

  EP1184366B1

文献信息

• Design, Synthesis, and Evaluation of Substituted Phenylpropanoic Acid Derivatives as Human Peroxisome Proliferator Activated Receptor Activators. Discovery of Potent and Human Peroxisome Proliferator Activated Receptor α Subtype-Selective Activators
  作者：Masahiro Nomura、Takahiro Tanase、Tomohiro Ide、Masaki Tsunoda、Masahiro Suzuki、Hideharu Uchiki、Koji Murakami、Hiroyuki Miyachi

  DOI：10.1021/jm0205144

  日期：2003.8.1

  Substituted phenylpropanoic acid derivatives were prepared as part of a search for subtype-selective human peroxisome proliferator activated receptor alpha (PPARalpha) activators. Structure-activity relationship studies indicated that the nature and the stereochemistry of the substituent at the alpha-position of the head part containing the carboxyl group, the distance between the carboxyl group and

  制备取代的苯基丙酸衍生物，作为寻找亚型选择性人过氧化物酶体增殖物激活受体α（PPARalpha）激活剂的一部分。构效关系研究表明，取代基在含有羧基的头部的α位，羧基与中心苯环之间的距离，中心苯环与苯环之间的连接基团的位置和立体化学特征。远端苯环和分子远端疏水尾部的取代基在确定PPAR亚型反式激活的效力和选择性中都起着关键作用。这项研究已导致鉴定出有效和人源的PPARalpha选择性旋光性α-烷基苯基丙酸衍生物，
• Substituted phenylpropionic acid derivatives as agonists to human peroxisome proliferator-activated receptor (PPAR) &agr;
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06506797B1

  公开（公告）日：2003-01-14

  The invention provides novel substituted phenylpropanoic acid derivatives that activate by binding to receptor as ligands of human peroxisome preliferant-activated receptor &agr; (PPAR&agr;), and exhibit potent decreasing action on lipids in blood (cholesterol and triglyceride). It relates to a substituted phenylpropanoic acid derivatives represented by a general formula (1), their pharmaceutically acceptable salts and their hydrates, and processes for preparing them.

  本发明提供了一种新型取代苯丙酸衍生物，它们通过作为人类过氧化物酶体增殖物激活受体α（PPARα）的配体结合而激活，并表现出强效的降低血液中脂质（胆固醇和甘油三酯）的作用。它涉及一种由通式（1）表示的取代苯丙酸衍生物，它们的药学上可接受的盐和水合物，以及制备它们的方法。
• Novel stable crystals of substituted phenylpropionic acid derivative and process for producing the same
  申请人：Orita Kazuo

  公开号：US20050228050A1

  公开（公告）日：2005-10-13

  Preparation of (S)-2-[[3-[N-[4-[(4-fluorophenoxy)phenyl]methyl]carbamoyl]-4-methoxyphenyl]methyl]butanoic acid (referred to as compound (I)) on an industrial scale lies in the finding of crystals homogeneous and excellent in the stability and the establishment of a preparative process thereof. Novel crystals of compound (I) homogeneous and excellent in the stability characterized by exhibiting the diffraction angles (2θ) at at least 17.7°, 19.0° and 24.1° in the X-ray powder diffraction are provided by recrystallizing from an alcoholic solvent and purifying by acid-base treatment.

  (S)-2-[[3-[N-[4-[(4-氟苯氧)苯基]甲基]氨基甲酰]-4-甲氧基苯基]甲基]丁酸（简称化合物(I)）的工业规模制备在于发现晶体的均匀性和稳定性，并建立其制备过程。通过从醇类溶剂中重新结晶并通过酸碱处理纯化，提供了表现出X射线粉末衍射中至少17.7°、19.0°和24.1°的衍射角度（2θ）的化合物(I)的新晶体，这些晶体均匀且稳定。
• Stable crystals of substituted phenylpropionic acid derivative and process for producing the same
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US07279596B2

  公开（公告）日：2007-10-09

  Preparation of (S)-2-[[3-[N-[4-[(4-fluorophenoxy)phenyl]methyl]carbamoyl]-4-methoxyphenyl]methyl]butanoic acid (referred to as compound (I)) on an industrial scale lies in the finding of crystals homogeneous and excellent in the stability and the establishment of a preparative process thereof. Novel crystals of compound (I) homogeneous and excellent in the stability characterized by exhibiting the diffraction angles (2θ) at at least 17.7°, 19.0° and 24.1° in the X-ray powder diffraction are provided by recrystallizing from an alcoholic solvent and purifying by acid-base treatment.

  (S)-2-[[3-[N-[4-[(4-氟苯氧)苯基]甲基]氨基甲酰]-4-甲氧基苯基]甲基]丁酸（简称化合物（I））的工业规模制备在于发现晶体在稳定性方面均匀且优秀，并建立其制备过程。通过从醇溶剂中重结晶并通过酸碱处理纯化，提供了在X射线粉末衍射中显示至少在17.7°、19.0°和24.1°处的衍射角（2θ）的化合物（I）新晶体，其均匀且稳定。
• NOVEL STABLE CRYSTALS OF SUBSTITUTED PHENYLPROPIONIC ACID DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP1462439B1

  公开（公告）日：2008-03-26