(S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide | 865839-06-1

• 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: (S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
• CAS: 865839-06-1
• 化学式: C₁₇H₂₉N₃O₅
• 分子量: 355.434
• InChiKey: JGLLCGABBJVUBG-GKSGUAPZSA-N

物化性质

• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide 、 3-氯-4-氨基苯甲酸 生成 N-(4-氨基-3-氯苯甲酰基)-3-甲基-L-缬氨酰-N-[(2R,3S)-2-乙氧基四氢-5-氧代-3-呋喃基]-L-脯氨酰胺
  参考文献：
  名称：

  Development of a Novel Pd-Catalyzed N-Acyl Vinylogous Carbamate Synthesis for the Key Intermediate of ICE Inhibitor VX-765

  摘要：

  A novel Pd-catalyzed coupling of Cbz-protected proline amide with 4-bromo-5-ethoxyfuran-2(5H)-one was developed for the synthesis of the P1-P2 unit (5) of VX-765. The process afforded quantitative coupling in the presence of water, providing a 1:1 mixture of 5 and its ethoxy epimer epi-5. Compound 5 was isolated as a single diastereomer via fractional crystallization, which was stereoselectively converted to 17 via hydrogenation, and subsequently transformed to VX-765. Nine examples of the Pd coupling are presented with yields ranging from 76-98%.

  DOI：

  10.1021/ol702532h
• 作为产物：
  描述：

  benzyl (2S)-1-((2S)-2-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-ylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate 在 20% Pd(OH)2 on carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  [EN] CASPASE INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE LA CASPASE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2005085236A3

文献信息

• Processes and intermediates
  申请人：Tanoury Gerald J.

  公开号：US20090048429A1

  公开（公告）日：2009-02-19

  The invention relates to processes and compounds useful for producing modified aspartic acid derivatives, such as aspartic acid aldehyde moieties. Aspartic acid derivatives are useful for preparing caspase inhibitors and/or prodrugs thereof.

  本发明涉及用于生产改性天冬氨酸衍生物的过程和化合物，例如天冬氨酸醛基团。天冬氨酸衍生物可用于制备半胱氨酸蛋白酶抑制剂和/或其前药。
• Processes and Intermediates
  申请人：Tanoury Gerald J.

  公开号：US20110071298A1

  公开（公告）日：2011-03-24

  The invention relates to processes and compounds useful for producing modified aspartic acid derivatives, such as aspartic acid aldehyde moieties. Aspartic acid derivatives are useful for preparing caspase inhibitors and/or prodrugs thereof.

  本发明涉及用于生产改性天冬氨酸衍生物的过程和化合物，例如天冬氨酸醛基团。天冬氨酸衍生物可用于制备卡斯帕酶抑制剂和/或其前药。
• PROCESSES AND INTERMEDIATES
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20130066083A1

  公开（公告）日：2013-03-14

  The invention relates to processes and compounds useful for producing modified aspartic acid derivatives, such as aspartic acid aldehyde moieties. Aspartic acid derivatives are useful for preparing caspase inhibitors and/or prodrugs thereof.

  本发明涉及用于生产改性天冬氨酸衍生物的过程和化合物，如天冬氨酸醛基团。天冬氨酸衍生物可用于制备半胱氨酸蛋白酶抑制剂和/或其前药。
• Process and intermediates for the preparation of aspartic acetal caspase ihnhibitors
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2399916A1

  公开（公告）日：2011-12-28

  The invention relates to a process of producing a compound of comprising purifying a mixture of wherein R8 is a protecting group, and purifying includes chromatographing, selectively crystallizing, or dynamically crystallizing the mixture.

  本发明涉及 一种生产下列化合物的工艺 的混合物，包括提纯 其中 R8 是保护基团，纯化包括对混合物进行色谱分析、选择性结晶或动态结晶。
• [EN] CASPASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA CASPASE ET LEURS UTILISATIONS
  申请人：VERTEX PHARMA

  公开号：WO2005085236A3

  公开（公告）日：2005-10-20