4-{(E)-3-[(R)-3-((S)-1-Ethoxycarbonylmethyl-prop-2-ynylcarbamoyl)-piperidin-1-yl]-3-oxo-propenyl}-piperidine-1-carboxylic acid tert-butyl ester | 183804-89-9

• 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: 4-{(E)-3-[(R)-3-((S)-1-Ethoxycarbonylmethyl-prop-2-ynylcarbamoyl)-piperidin-1-yl]-3-oxo-propenyl}-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-beta-alanine ethyl ester；tert-butyl 4-[(E)-3-[(3R)-3-[[(3S)-5-ethoxy-5-oxopent-1-yn-3-yl]carbamoyl]piperidin-1-yl]-3-oxoprop-1-enyl]piperidine-1-carboxylate
• CAS: 183804-89-9
• 化学式: C₂₆H₃₉N₃O₆
• 分子量: 489.612
• InChiKey: RBASQHVTFZFAAX-VRDGUJSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{(E)-3-[(R)-3-((S)-1-Ethoxycarbonylmethyl-prop-2-ynylcarbamoyl)-piperidin-1-yl]-3-oxo-propenyl}-piperidine-1-carboxylic acid tert-butyl ester 在 lithium hydroxide 、 盐酸 、 Diaion HP₂₀(R) 作用下， 以 乙酸乙酯 为溶剂， 以69%的产率得到FR184764
  参考文献：
  名称：

  An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764

  摘要：

  An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764 was achieved. The key intermediate, an optically active ethynyl beta-amino ester, was synthesized efficiently by utilizing a lipase catalyzed kinetic resolution step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.157
• 作为产物：
  描述：

  (R)-3-哌啶甲酸乙酯 在 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 4-{(E)-3-[(R)-3-((S)-1-Ethoxycarbonylmethyl-prop-2-ynylcarbamoyl)-piperidin-1-yl]-3-oxo-propenyl}-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764

  摘要：

  An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764 was achieved. The key intermediate, an optically active ethynyl beta-amino ester, was synthesized efficiently by utilizing a lipase catalyzed kinetic resolution step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.157

文献信息

• N-acylpiperidinylcarbonylaminocarboxylic acids and their use as glycoprotein IIb/IIIa antagonists and fibrinogen-blood platelets binding inhibitors
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06384028B1

  公开（公告）日：2002-05-07

  &bgr;-alanine compounds or a pharmaceutically acceptable salt thereof, which is useful as a glycoprotein IIB/IIIa antagonist, inhibitor of blood platelet aggregation and inhibitor of the binding of fibrinogen to blood platelet; a composition containing the same, a process for the preparation of the compound, and a process for the treatment of diseases caused by thrombus formation, for example, are provided.

  本发明提供了一种&bgr;-丙氨酸化合物或其药学上可接受的盐，该化合物可用作糖蛋白IIB/IIIa拮抗剂、血小板聚集抑制剂和纤维蛋白原与血小板结合的抑制剂；一种含有该化合物的组合物、制备该化合物的方法以及用于治疗由血栓形成引起的疾病的方法。
• An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764
  作者：Toshio Yamanaka、Mitsuru Ohkubo、Fumie Takahashi、Masayuki Kato

  DOI：10.1016/j.tetlet.2004.01.157

  日期：2004.3

  An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764 was achieved. The key intermediate, an optically active ethynyl beta-amino ester, was synthesized efficiently by utilizing a lipase catalyzed kinetic resolution step. (C) 2004 Elsevier Ltd. All rights reserved.