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 | 944716-71-6

• 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
• 中文名称: 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
• 英文名称: (2S,3S)-N-cyclopropyl-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid amide
• 英文别名: Carbamic acid, N-[(1S)-1-[(1S)-2-(cyclopropylamino)-1-hydroxy-2-oxoethyl]butyl]-, 1,1-dimethylethyl ester；tert-butyl N-[(2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate
• CAS: 944716-71-6
• 化学式: C₁₄H₂₆N₂O₄
• 分子量: 286.371
• InChiKey: DPFCMHQQTKBKAX-QWRGUYRKSA-N

物化性质

• 沸点：
  486.9±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  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 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 特拉匹韦中间体2
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3/4A: α-Ketoamide based macrocyclic inhibitors

  摘要：

  A novel series of hepatitis C virus (HCV) NS3/4A protease inhibitors bearing a P2-P4 macrocycle and a P1-P1' alpha-ketoamide serine trap is reported. The NS3 protease, which is essential for viral replication, is considered one of the most attractive targets for developing novel anti-HCV therapies. The optimization of both the macrocycle and the warhead portions led to the discovery of compounds 8b and 8g with a good activity both in the enzyme as well as in the cell based (replicon) assays with favorable PK profile in a preclinical species. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.079
• 作为产物：
  描述：

  2-羟基-, (3s)- 、 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 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 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：

  Inhibitors of hepatitis C virus NS3/4A: α-Ketoamide based macrocyclic inhibitors

  摘要：

  A novel series of hepatitis C virus (HCV) NS3/4A protease inhibitors bearing a P2-P4 macrocycle and a P1-P1' alpha-ketoamide serine trap is reported. The NS3 protease, which is essential for viral replication, is considered one of the most attractive targets for developing novel anti-HCV therapies. The optimization of both the macrocycle and the warhead portions led to the discovery of compounds 8b and 8g with a good activity both in the enzyme as well as in the cell based (replicon) assays with favorable PK profile in a preclinical species. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.079

文献信息

• 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。
• EP1988073
  申请人：——

  公开号：——

  公开（公告）日：——
• US8183413B2
  申请人：——

  公开号：US8183413B2

  公开（公告）日：2012-05-22