(2S,3S)-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid | 944716-69-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid
• 英文别名: (2S,3S)-N-tert-butoxycarbonyl-3-amino-2-hydroxy-hexanoic acid；(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid；(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 944716-69-2
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: RPIFNVNQWSPEMY-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid 、 环丙胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 22.0h， 以90%的产率得到N-[(1S)-1-[(1S)-2-(环丙基氨基)-1-羟基-2-氧代乙基]丁基]氨基甲酸叔丁酯
  参考文献：
  名称：

  EP1988073

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl (4S,5S)-2-methyl-4-propyl-4,5-dihydro-1,3-oxazole-5-carboxylate 、 二碳酸二叔丁酯 在 盐酸 、 水 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以78%的产率得到(2S,3S)-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid
  参考文献：
  名称：

  EP2039689

  摘要：

  公开号：

文献信息

• 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。
• Process for Production of Beta-Amino-Alpha-Hydroxy Carbonxamide Derivative
  申请人：Kishimoto Narumi

  公开号：US20090312577A1

  公开（公告）日：2009-12-17

  Provided is a process for production of a β-amino-α-hydroxy carboxamide derivative that is important in production of drugs or the like. In the presence of a predetermined solvent, a β-(N-protected)amino-α-hydroxycarboxylic acid is reacted with an amine to conversion to a β-(N-protected)amino-α-hydroxy carboxamide derivative; then the derivative is deprotected for conversion to a β-amino-α-hydroxy carboxamide derivative; and the derivative is crystallized using a protic solvent to obtain a crystal. The high-purity β-amino-α-hydroxy carboxamide derivative can be stably produced on an industrial scale by the process.

  提供了一种用于生产药物或类似物质中重要的β-氨基-α-羟基羧酰胺衍生物的生产工艺。在预定溶剂的存在下，将β-(N-保护)氨基-α-羟基羧酸与胺反应，转化为β-(N-保护)氨基-α-羟基羧酰胺衍生物；然后去保护基，转化为β-氨基-α-羟基羧酰胺衍生物；并使用质子溶剂结晶，以获得晶体。该工艺可以稳定地在工业规模上生产高纯度的β-氨基-α-羟基羧酰胺衍生物。
• Process for production of β-amino-α-hydroxy carboxamide derivative
  申请人：Kaneka Corporation

  公开号：US08183413B2

  公开（公告）日：2012-05-22

  Provided is a process for production of a β-amino-α-hydroxy carboxamide derivative that is important in production of drugs or the like. In the presence of a predetermined solvent, a β-(N-protected)amino-α-hydroxycarboxylic acid is reacted with an amine to conversion to a β-(N-protected)amino-α-hydroxy carboxamide derivative; then the derivative is deprotected for conversion to a β-amino-α-hydroxy carboxamide derivative; and the derivative is crystallized using a protic solvent to obtain a crystal. The high-purity β-amino-α-hydroxy carboxamide derivative can be stably produced on an industrial scale by the process.

  提供的是一种生产β-氨基-α-羟基羧酰胺衍生物的方法，该方法在制药或类似领域中非常重要。在预定的溶剂存在下，β-(N-保护)氨基-α-羟基羧酸与胺反应，转化为β-(N-保护)氨基-α-羟基羧酰胺衍生物；然后去保护基，转化为β-氨基-α-羟基羧酰胺衍生物；最后使用质子溶剂结晶，得到晶体。该方法可以在工业规模下稳定地生产高纯度的β-氨基-α-羟基羧酰胺衍生物。
• PROCESS FOR PRODUCTION OF BETA-AMINO-ALPHA-HYDROXY ACID AMIDE DERIVATIVE
  申请人：Kaneka Corporation

  公开号：EP1988073A1

  公开（公告）日：2008-11-05

  Provided is a process for production of a β-amino-α-hydroxy carboxamide derivative that is important in production of drugs or the like. In the presence of a predetermined solvent, a β-(N-protected)amino-α-hydroxycarboxylic acid is reacted with an amine to conversion to a β-(N-protected)amino-α-hydroxy carboxamide derivative; then the derivative is deprotected for conversion to a β-amino-α-hydroxy carboxamide derivative; and the derivative is crystallized using a protic solvent to obtain a crystal. The high-purity β-amino-α-hydroxy carboxamide derivative can be stably produced on an industrial scale by the process.

  本发明提供了一种β-氨基-α-羟基羧酰胺衍生物的生产工艺，这种衍生物在药物或类似物的生产中非常重要。在预先确定的溶剂存在下，β-（N-保护）氨基-α-羟基羧酸与胺反应，转化为β-（N-保护）氨基-α-羟基羧酰胺衍生物；然后对该衍生物进行脱保护，转化为β-氨基-α-羟基羧酰胺衍生物；再使用质子溶剂对该衍生物进行结晶，得到晶体。通过该工艺可在工业规模上稳定生产高纯度的 β-氨基-α-羟基羧酰胺衍生物。
• 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。