(S)-4-benzyl-3-((S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoyl)oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-4-benzyl-3-((S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoyl)oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoyl]-1,3-oxazolidin-2-one
• 化学式: C₂₅H₂₁BrClNO₃
• 分子量: 498.804
• InChiKey: VSHHMWPXQIHNMM-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoyl)oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(S)-2-(3-溴苯基)-3-(4-氯苯基)丙酸
  参考文献：
  名称：

  Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent

  摘要：

  Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB I R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursued by Merck toward obesity market. Merck intends to file for FDA approval of taranabant in 2008. In order to overcome practical difficulty involved in lab-scale preparation of taranabant with a dynamic kinetic resolution procedure developed by Merck's process group, we developed a 'user-friendly' method to install stereogenic centers by adopting Evans asymmetry chemistry. This method allowed us to prepare readily sub-gram scale of the target compound in a convenient way. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.056
• 作为产物：
  描述：

  (S)-4-benzyl-3-(2-(3-bromophenyl)acetyl)oxazolidin-2-one 、 4-氯苄溴 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(S)-4-benzyl-3-((S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent

  摘要：

  Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB I R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursued by Merck toward obesity market. Merck intends to file for FDA approval of taranabant in 2008. In order to overcome practical difficulty involved in lab-scale preparation of taranabant with a dynamic kinetic resolution procedure developed by Merck's process group, we developed a 'user-friendly' method to install stereogenic centers by adopting Evans asymmetry chemistry. This method allowed us to prepare readily sub-gram scale of the target compound in a convenient way. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.056

文献信息

• Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent
  作者：Min-ah Kim、Jong Yup Kim、Kwang-Seop Song、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.tet.2007.10.056

  日期：2007.12

  Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB I R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursued by Merck toward obesity market. Merck intends to file for FDA approval of taranabant in 2008. In order to overcome practical difficulty involved in lab-scale preparation of taranabant with a dynamic kinetic resolution procedure developed by Merck's process group, we developed a 'user-friendly' method to install stereogenic centers by adopting Evans asymmetry chemistry. This method allowed us to prepare readily sub-gram scale of the target compound in a convenient way. (c) 2007 Elsevier Ltd. All rights reserved.