2-[5-[(1S)-1-[(2-amino-2-methylpropanoyl)amino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl N-(4-hydroxybutyl)carbamate;(2R)-2-hydroxy-2-phenylacetic acid | 1154710-54-9

• 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: 2-[5-[(1S)-1-[(2-amino-2-methylpropanoyl)amino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl N-(4-hydroxybutyl)carbamate;(2R)-2-hydroxy-2-phenylacetic acid
• CAS: 1154710-54-9
• 化学式: C₈H₈O₃*C₂₁H₃₃N₇O₅
• 分子量: 615.687
• InChiKey: ZLCCGGXVKKYNFK-QEKUCLETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  224
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-[5-[(1S)-1-[(2-amino-2-methylpropanoyl)amino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl N-(4-hydroxybutyl)carbamate;(2R)-2-hydroxy-2-phenylacetic acid 在 potassium phosphate 、 水 、 磷酸 作用下， 以 乙酸乙酯 为溶剂， 反应 5.25h， 以81.2%的产率得到C₂₁H₃₃N₇O₅*H₃O₄P
  参考文献：
  名称：

  Process Research and Development for a Tetrazole-Based Growth Hormone Secretagogue (GHS) Pharmaceutical Development Candidate

  摘要：

  BMS-317180 (1) is a potent, orally active agonist of the human growth hormone secretagogue (GHS) receptor. This manuscript details the process research and development efforts that enabled the synthesis of the phosphate salt of 1 on a multi-kilogram scale. Key considerations in the development of this process focused on safe execution and the requirement for telescoped synthetic transformations (i.e., without isolation of intermediate products) to contend with a lack of suitably crystalline products.

  DOI：

  10.1021/jo9003508
• 作为产物：
  描述：

  2-[5-[(1S)-1-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl N-(4-hydroxybutyl)carbamate 、 D-扁桃酸 在 盐酸 、 水 、 potassium phosphate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 6.75h， 以2.38 kg的产率得到2-[5-[(1S)-1-[(2-amino-2-methylpropanoyl)amino]-2-phenylmethoxyethyl]tetrazol-1-yl]ethyl N-(4-hydroxybutyl)carbamate;(2R)-2-hydroxy-2-phenylacetic acid
  参考文献：
  名称：

  Process Research and Development for a Tetrazole-Based Growth Hormone Secretagogue (GHS) Pharmaceutical Development Candidate

  摘要：

  BMS-317180 (1) is a potent, orally active agonist of the human growth hormone secretagogue (GHS) receptor. This manuscript details the process research and development efforts that enabled the synthesis of the phosphate salt of 1 on a multi-kilogram scale. Key considerations in the development of this process focused on safe execution and the requirement for telescoped synthetic transformations (i.e., without isolation of intermediate products) to contend with a lack of suitably crystalline products.

  DOI：

  10.1021/jo9003508

文献信息

• Process Research and Development for a Tetrazole-Based Growth Hormone Secretagogue (GHS) Pharmaceutical Development Candidate
  作者：Akin H. Davulcu、Douglas D. McLeod、Jun Li、Kishta Katipally、Adam Littke、Wendel Doubleday、Zhongmin Xu、Cary W. McConlogue、Chiajen J. Lai、Margaret Gleeson、Mark Schwinden、Rodney L. Parsons

  DOI：10.1021/jo9003508

  日期：2009.6.5

  BMS-317180 (1) is a potent, orally active agonist of the human growth hormone secretagogue (GHS) receptor. This manuscript details the process research and development efforts that enabled the synthesis of the phosphate salt of 1 on a multi-kilogram scale. Key considerations in the development of this process focused on safe execution and the requirement for telescoped synthetic transformations (i.e., without isolation of intermediate products) to contend with a lack of suitably crystalline products.