(2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide | 950483-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide
• 英文别名: (2S,3R)-N-cyclopropyl-3-propyloxirane-2-carboxamide
• CAS: 950483-64-4
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: ARDZPNHBMYHPHZ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide 、 乙腈 在 三氟化硼乙醚 作用下， 反应 4.0h， 以90%的产率得到(4S,5S)-N-cyclopropyl-2-methyl-4-propyl-4,5-dihydro-1,3-oxazole-5-carboxamide
  参考文献：
  名称：

  EP2039689

  摘要：

  公开号：
• 作为产物：
  描述：

  环丙胺 、 (3R,2S)-3-propyloxirane-2-carboxylic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以53%的产率得到(2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide
  参考文献：
  名称：

  EP2039689

  摘要：

  公开号：

文献信息

• PROCESSES AND INTERMEDIATES
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20130172276A1

  公开（公告）日：2013-07-04

  The invention relates to compounds and processes useful for the preparation of protease inhibitors, particularly serine protease inhibitors. The protease inhibitors are useful for treatment of HCV infections.

  本发明涉及化合物和用于制备蛋白酶抑制剂的方法，特别是丝氨酸蛋白酶抑制剂。这些蛋白酶抑制剂对治疗HCV感染非常有用。
• Processes and intermediates for preparing steric compounds
  申请人：Tanoury J. Gerald

  公开号：US20070244334A1

  公开（公告）日：2007-10-18

  This invention relates to processes and intermediates for the preparation of an alpha-amino beta-hydroxy acid of Formula 1 wherein the variables R 1 , R′ 1 and R 2 are defined herein and the compound of Formula 1 has an enantiomeric excess (ee) of 55% or greater.

  本发明涉及制备式1的α-氨基β-羟基酸的过程和中间体，其中变量R1、R′1和R2在此定义，式1的化合物的对映体过量（ee）为55％或更高。
• Process for production of optically active-3-amino-2-hydroxypropionic cyclopropylamide derivatives and salts thereof
  申请人：Mori Kohei

  公开号：US20100048909A1

  公开（公告）日：2010-02-25

  An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

  本申请的目标是提供一种工业实用的方法，从廉价易得的起始物质中生产出光学活性的3-氨基-2-羟基丙酸环丙酰胺衍生物或其盐。该衍生物或其盐可用作药物的中间体。本申请还旨在提供该衍生物的有用中间体。该目标通过以下方法实现。首先，对易得的2-卤代-3-酮丙酸衍生物进行不对称还原，然后环氧化，以产生光学活性的环氧羧酸衍生物。接下来，通过与环丙胺反应将该衍生物转化为光学活性的环氧酰胺衍生物，然后与腈反应得到光学活性的噁唑烷酰胺衍生物。随后，对噁唑烷骨架进行选择性酸性溶解，得到光学活性的3-氨基-2-羟基丙酸环丙酰胺衍生物或其盐。
• PROCESSES AND INTERMEDIATES FOR PREPARING STERIC COMPOUNDS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20130131359A1

  公开（公告）日：2013-05-23

  This invention relates to processes and intermediates for the preparation of an alpha-amino beta-hydroxy acid of Formula 1 wherein the variables R 1 , R′ 1 and R 2 are defined herein and the compound of Formula 1 has an enantiomeric excess (ee) of 55% or greater.

  本发明涉及一种制备公式1中α-氨基β-羟基酸的方法和中间体，其中变量R1、R′1和R2在此处定义，公式1的化合物具有55%或更高的对映体过量（ee）。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2 -HYDROXYPROPIONIC CYCLOPROPYLAMIDE DERIVATIVES AND SALTS THEREOF
  申请人：Kaneka Corporation

  公开号：EP2039689A1

  公开（公告）日：2009-03-25

  An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

  本申请的目的是提供一种工业上可行的方法，利用廉价易得的起始原料生产具有光学活性的 3-氨基-2-羟基丙酰基环丙基酰胺衍生物或其盐。该衍生物或其盐可用作药物的中间体。本申请的另一个目的是提供一种有用的衍生物中间体。通过以下方法可以达到目的。首先，将一种易得的 2-卤代-3-氧代丙酸衍生物进行不对称还原，然后环氧化，生成一种具有光学活性的环氧羧酸衍生物。接着，该衍生物与环丙胺反应转化为光学活性环氧酰胺衍生物，然后与腈反应得到光学活性噁唑啉酰胺衍生物。随后，对噁唑啉骨架进行选择性酸溶解，得到具有光学活性的 3-氨基-2-羟基丙酸环丙基酰胺衍生物或其盐。