(3S)-glycyl-3-(3-bromo-5-chloro-2-hydroxyphenyl)-β-alanine ethyl ester monohydrochloride | 243136-09-6

• 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: (3S)-glycyl-3-(3-bromo-5-chloro-2-hydroxyphenyl)-β-alanine ethyl ester monohydrochloride
• CAS: 243136-09-6
• 化学式: C₁₃H₁₆BrClN₂O₄*ClH
• 分子量: 416.099
• InChiKey: WZFGZTHHKGYZPD-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101.65
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-((5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzoic acid 、 (3S)-glycyl-3-(3-bromo-5-chloro-2-hydroxyphenyl)-β-alanine ethyl ester monohydrochloride 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ethyl (3S)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-[[2-[[3-hydroxy-5-[(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino]benzoyl]amino]acetyl]amino]propanoate
  参考文献：
  名称：

  Pilot-Plant Preparation of an α_vβ₃ Integrin Antagonist. Part 3. Process Research and Development of a Diisopropylcarbodiimide and Catalytic 1-Hydroxybenzotriazole Peptide Coupling

  摘要：

  Studies directed toward the process research, development, and scale-up preparation of the potential alpha(v)beta(3) integrin antagonist 1 are described. A convergent approach is detailed wherein tetrahydropyrimidine hydroxybenzoic acid 2 is linked to the beta-amino acid ester 3 via a , catalytic HOBt coupling reaction. Saponification of the resulting ethyl ester, isolation of the corresponding zwitterion, H3PO4 salt formation, crystallization, and acetonitrile-to-acetone exchange give rise to I as a crystalline monohydrate in 67% overall yield from 4.

  DOI：

  10.1021/op900173f
• 作为产物：
  描述：

  (3S)-N-[(1,1-dimethylethoxy)carbonyl]glycyl-3-[3-bromo-5-chloro-2-hydroxyphenyl]-β-alanine ethyl ester 在 乙醇 、 乙酰氯 作用下， 以93%的产率得到(3S)-glycyl-3-(3-bromo-5-chloro-2-hydroxyphenyl)-β-alanine ethyl ester monohydrochloride
  参考文献：
  名称：

  Pilot-Plant Preparation of an α_vβ₃ Integrin Antagonist. Part 3. Process Research and Development of a Diisopropylcarbodiimide and Catalytic 1-Hydroxybenzotriazole Peptide Coupling

  摘要：

  Studies directed toward the process research, development, and scale-up preparation of the potential alpha(v)beta(3) integrin antagonist 1 are described. A convergent approach is detailed wherein tetrahydropyrimidine hydroxybenzoic acid 2 is linked to the beta-amino acid ester 3 via a , catalytic HOBt coupling reaction. Saponification of the resulting ethyl ester, isolation of the corresponding zwitterion, H3PO4 salt formation, crystallization, and acetonitrile-to-acetone exchange give rise to I as a crystalline monohydrate in 67% overall yield from 4.

  DOI：

  10.1021/op900173f