(3S)-N-[(1,1-dimethylethoxy)carbonyl]glycyl-3-[3-bromo-5-chloro-2-hydroxyphenyl]-β-alanine ethyl ester | 243136-08-5

• 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)-N-[(1,1-dimethylethoxy)carbonyl]glycyl-3-[3-bromo-5-chloro-2-hydroxyphenyl]-β-alanine ethyl ester
• 英文别名: ethyl (3S)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-3-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoate
• CAS: 243136-08-5
• 化学式: C₁₈H₂₄BrClN₂O₆
• 分子量: 479.755
• InChiKey: IKEXWBCPNKGNNS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (3S)-3-amino-3-(3-bromo-5-chloro-2-hydroxyphenyl)propionic acid ethyl ester p-toluenesulfonate 、 BOC-甘氨酸-N-羟基琥柏酰亚胺酯 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以66%的产率得到(3S)-N-[(1,1-dimethylethoxy)carbonyl]glycyl-3-[3-bromo-5-chloro-2-hydroxyphenyl]-β-alanine ethyl ester
  参考文献：
  名称：

  Pilot-Plant Preparation of an α_vβ₃ Integrin Antagonist: Process Development of a Carbonyldiimidazole Peptide Coupling

  摘要：

  The process development of a peptide coupling with CDI is discussed. Various solvents, addition orders, stoichiometries, and reaction temperatures were investigated. A reliable crystallization procedure was also developed. The new process was piloted to provide 342 kg of product in two batches with an average 85% yield and 99% assay.

  DOI：

  10.1021/op8002213