[1S-[1S,3S,4S]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide 5-Oxo-L-proline salt | 192726-06-0

• 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: [1S-[1S,3S,4S]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide 5-Oxo-L-proline salt
• 英文别名: (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt；(2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-1-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane S-pyroglutamic acid salt；(2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydropyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane 5-oxo-L-proline salt；N-(4-amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid；(2S)-N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide;(2S)-5-oxopyrrolidine-2-carboxylic acid
• CAS: 192726-06-0
• 化学式: C₅H₇NO₃*C₂₇H₃₈N₄O₃
• 分子量: 595.739
• InChiKey: XTNBASMLUMHKST-JBINCMMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [1S-[1S,3S,4S]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide 5-Oxo-L-proline salt 、 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以92%的产率得到洛匹那韦
  参考文献：
  名称：

  一种制备洛匹那韦新方法

  摘要：

  一种制备洛匹那伟(I)的新方法其由式(II)所示化合物与式(III)所示化合物进行缩合反应缩合反应条件温和，在室温下进行即可，无需加热或降温；该制备方法无需特殊化学试剂，均为实验室常用的溶剂和试剂，总收率高于85％，优选高于90％，在某些实施例中产率达到96％，特别适合于工业化生产。

  公开号：

  CN111018791B
• 作为产物：
  描述：

  (2S)-(1-四氢嘧啶-2-酮)-3-甲基丁酸 在 咪唑 、 氯化亚砜 、 5%-palladium/activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 [1S-[1S,3S,4S]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide 5-Oxo-L-proline salt
  参考文献：
  名称：

  Synthesis of HIV Protease Inhibitor ABT-378 (Lopinavir)

  摘要：

  A large scale process for the synthesis of HIV protease inhibitor candidate ABT-378 has been developed which utilizes an intermediate common to the synthesis of ritonavir, Abbott's first generation compound, The synthesis relies on the sequential acylation of this intermediate which is carried through as a mixture of diastereomers until the penultimate step. A synthesis of acid 5, derived from L-valine, is also reported.

  DOI：

  10.1021/op990202j

文献信息

• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP1170289A2

  公开（公告）日：2002-01-09

  A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

  披露了一种包含公式（II）取代基的化合物，作为一种HIV蛋白酶抑制剂。还披露了用于制造此类化合物的中间体以及制造此类中间体的过程。
• [EN] AN IMPROVED PROCESS FOR PREPARATION OF LOPINAVIR AND ITS INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DU LOPINAVIR ET DE SES INTERMÉDIAIRES
  申请人：LAURUS LABS LTD

  公开号：WO2019186522A1

  公开（公告）日：2019-10-03

  The present invention generally relates to an improved process for preparation of lopinavir and its intermediates through formation of tartrate salt of compound of Formula (III).

  本发明一般涉及通过形成化合物的酒石酸盐的改进过程，以制备洛匹那韦及其中间体。
• PROCESS FOR THE PREPARATION OF SUBSTANTIALLY PURE (2S,3S,5S)-5-AMINO-2-N,N-DIBENZYLAMINO-3-HYDROXY-1,6-DIPHENYLHEXANE
  申请人：Ambati V Raghava Reddy

  公开号：US20100317855A1

  公开（公告）日：2010-12-16

  The present invention relates to the purification of (2S,3S,5S)-5-amino-2-N,N-dibenzylamino-3-hydroxy-1,6-diphenylhexane (III) by making its crystalline acid addition salt, which can be used as such to produce Lopinavir/Ritonavir with high purity and yield. Formula III

  本发明涉及通过制备其结晶酸加盐物来纯化(2S,3S,5S)-5-氨基-2-N,N-二苯基氨基-3-羟基-1,6-二苯基己烷(III)，该物质可直接用于生产高纯度和产率的洛匹那韦/利托那韦。公式 III
• Processes and intermediates for preparing retroviral protease inhibitors
  申请人：Abbott Laboratories

  公开号：US06372905B1

  公开（公告）日：2002-04-16

  The instant invention provides processes and intermediates employed in the synthesis of ((2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)-amino-3-hydroxy-5-(2S-(1-tetrahydropyrimid-2-onyl)-3-methyl-butanoyl)amino-1,6-diphenylhexane and analogs thereof.

  本发明提供了用于合成((2S,3S,5S)-2-(2,6-二甲基苯氧乙酰)氨基-3-羟基-5-(2S-(1-四氢嘧啶-2-酰基)-3-甲基丁酰基)氨基-1,6-二苯基己烷及其类似物的过程和中间体。
• Synthesis of HIV Protease Inhibitor ABT-378 (Lopinavir)
  作者：Eric J. Stoner、Arthur J. Cooper、Daniel A. Dickman、Lawrence Kolaczkowski、John E. Lallaman、Jih-Hua Liu、Patricia A. Oliver-Shaffer、Ketan M. Patel、Joseph B. Paterson、Daniel J. Plata、David A. Riley、Hing. L. Sham、Peter J. Stengel、Jien-Heh J. Tien

  DOI：10.1021/op990202j

  日期：2000.7.1

  A large scale process for the synthesis of HIV protease inhibitor candidate ABT-378 has been developed which utilizes an intermediate common to the synthesis of ritonavir, Abbott's first generation compound, The synthesis relies on the sequential acylation of this intermediate which is carried through as a mixture of diastereomers until the penultimate step. A synthesis of acid 5, derived from L-valine, is also reported.