benzyl (2S)-2-((2S)-2-ethoxy-5-oxo-2,5-dihydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate | 865838-96-6

• 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
• 英文名称: benzyl (2S)-2-((2S)-2-ethoxy-5-oxo-2,5-dihydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-[[(2S)-2-ethoxy-5-oxo-2H-furan-3-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 865838-96-6
• 化学式: C₁₉H₂₂N₂O₆
• 分子量: 374.393
• InChiKey: ABYYATZCXRICQU-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴-5-乙氧基-2(5H)-呋喃酮 、 Cbz-L-脯氨酸酰胺 在 palladium diacetate 十六烷基三甲基溴化铵 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 、 水 为溶剂， 反应 8.25h， 以33%的产率得到benzyl (2S)-2-((2R)-2-ethoxy-5-oxo-2,5-dihydrofuran-3-ylcarbamoyl)pyrrolidine-1-carboxylate
  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

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。
• PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF ASPARTIC ACETAL CASPASE INHIBITORS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP1725548B1

  公开（公告）日：2015-01-14