(2S,4R)-N-tert-butyl-4-(pyridin-4-ylmethoxy)piperidine-2-carboxamide | 190508-41-9

• 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: (2S,4R)-N-tert-butyl-4-(pyridin-4-ylmethoxy)piperidine-2-carboxamide
• CAS: 190508-41-9
• 化学式: C₁₆H₂₅N₃O₂
• 分子量: 291.393
• InChiKey: IXNPNZDOIYBALJ-KGLIPLIRSA-N

物化性质

• 沸点：
  486.4±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N-tert-butyl-4-(pyridin-4-ylmethoxy)piperidine-2-carboxamide 在 N-甲基吗啉 、 盐酸 、 aluminum oxide 、 氯甲酸异丁酯 作用下， 反应 27.5h， 生成 N-[(2R)-1-[[(2S,3R)-4-[(2S,4R)-2-(tert-butylcarbamoyl)-4-(pyridin-4-ylmethoxy)piperidin-1-yl]-3-hydroxy-1-phenylbutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]quinoline-2-carboxamide
  参考文献：
  名称：

  Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor

  摘要：

  Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.

  DOI：

  10.1021/jo9702655
• 作为产物：
  描述：

  N-<(S)-2-phenylethyl>-(2S,4R)-4-hydroxypipecolic acid tert-butylamide 在 盐酸 、 氢气 、 sodium hydride 作用下， 15.0~25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (2S,4R)-N-tert-butyl-4-(pyridin-4-ylmethoxy)piperidine-2-carboxamide
  参考文献：
  名称：

  Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor

  摘要：

  Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.

  DOI：

  10.1021/jo9702655

文献信息

• Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor
  作者：Pierre L. Beaulieu、Pierre Lavallée、Abraham、Paul C. Anderson、Colette Boucher、Yves Bousquet、Jean-Simon Duceppe、James Gillard、Vida Gorys、Chantal Grand-Maître、Louis Grenier、Yvan Guindon、Ingrid Guse、Louis Plamondon、François Soucy、Serge Valois、Dominik Wernic、Christiane Yoakim

  DOI：10.1021/jo9702655

  日期：1997.5.1

  Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.