N-(1-benzylcarbamoyl-3-methyl-2-oxobutyl)-4-fluorobenzamide | 867309-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-benzylcarbamoyl-3-methyl-2-oxobutyl)-4-fluorobenzamide
• 英文别名: N-(1-Benzylcarbamoyl-3-methyl-2-oxo-butyl)-4-fluorobenzamide；N-[1-(benzylamino)-4-methyl-1,3-dioxopentan-2-yl]-4-fluorobenzamide
• CAS: 867309-02-2
• 化学式: C₂₀H₂₁FN₂O₃
• 分子量: 356.397
• InChiKey: XIAHTHBJSGPQBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-benzylcarbamoyl-3-methyl-2-oxobutyl)-4-fluorobenzamide 在 苯甲酸 、 三氟乙酸 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 tert-butyl (3R,5R)-7-[4-(benzylcarbamoyl)-2-(4-fluorophenyl)-5-propan-2-ylimidazol-1-yl]-3,5-dihydroxyheptanoate
  参考文献：
  名称：

  Preparation of a HMG-CoA Reductase Inhibitor via an Optimized Imidazole-Forming Condensation Reaction

  摘要：

  Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.

  DOI：

  10.1021/op800092e
• 作为产物：
  描述：

  2-(4-fluorobenzoylamino)-4-methyl-3-oxopentanoic acid benzyl ester 在 三乙胺 、 苄胺 作用下， 以 正庚烷 为溶剂， 反应 6.0h， 以80%的产率得到N-(1-benzylcarbamoyl-3-methyl-2-oxobutyl)-4-fluorobenzamide
  参考文献：
  名称：

  Preparation of a HMG-CoA Reductase Inhibitor via an Optimized Imidazole-Forming Condensation Reaction

  摘要：

  Development work toward an enabling synthesis of preparative scale batches of an imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by an imidazole-forming condensation reaction in which the yield was improved from 20% to >70% via modification of the solvent, acid, and amine equivalents. The step 2 acylation was improved, and a problematic benzyl ester in step 4 was converted into the corresponding benzyl amide to decrease trans-amidation during the step 5 imidazole formation. A highly effective salt formation and crystallization protocol was also developed.

  DOI：

  10.1021/op800092e

文献信息

• Novel imidazoles
  申请人：Bolton Louis Gary

  公开号：US20050239857A1

  公开（公告）日：2005-10-27

  Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

  提供了新型咪唑类化合物。这些化合物可用作HMGCo-A还原酶抑制剂。还提供了这些化合物的药物组合物。还提供了制备这些化合物的方法和使用这些化合物的方法。
• Novel pyrroles and imidazoles
  申请人：Bolton Louis Gary

  公开号：US20060287378A1

  公开（公告）日：2006-12-21

  Novel imidazoles and novel pyrroles are provided. Also provided are pharmaceutical compositions, methods of making and methods of using the compounds.

  本发明提供了新型咪唑和新型吡咯。同时，还提供了制药组合物、制备方法和使用该化合物的方法。
• WO2007/49121
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL IMIDAZOLES
  申请人：Warner-Lambert Company LLC

  公开号：EP1740549A2

  公开（公告）日：2007-01-10
• [EN] NOVEL IMIDAZOLES<br/>[FR] NOUVEAUX IMIDAZOLES
  申请人：BOLTON GARY LOUIS

  公开号：WO2005105079A2

  公开（公告）日：2005-11-10

  Novel imidazoles are provided. The compounds are useful as HMGCo-A Reductase Inhibitor. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.