tert-butyl N-[(2R)-1-(2-hydroxyethylamino)-1-oxo-3-phenylmethoxypropan-2-yl]carbamate | 295338-28-2

• 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: tert-butyl N-[(2R)-1-(2-hydroxyethylamino)-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 295338-28-2
• 化学式: C₁₇H₂₆N₂O₅
• 分子量: 338.404
• InChiKey: CRRHPOLYPWYTFD-CQSZACIVSA-N

物化性质

• 沸点：
  558.9±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-1-(2-hydroxyethylamino)-1-oxo-3-phenylmethoxypropan-2-yl]carbamate 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以3.85 g的产率得到2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]amino]ethyl acetate
  参考文献：
  名称：

  Discovery of a Tetrazole-Based Growth Hormone Secretagogue:  4-(Hydroxybutyl)carbamic Acid 2-{5-[1-(2-Amino-2-methylpropionylamino)-2- benzyloxyethyl]tetrazol-1-yl}ethyl Ester (BMS-317180)

  摘要：

  A tetrazole-based peptidomimetic 2 (BMS-317180) was discovered as a human growth hormone secretagogue (GHS). Compound 2 is a potent, novel, orally effective GHS that shows an excellent safety profile in preclinical studies. The compound was advanced into clinical development.

  DOI：

  10.1021/jm7010595
• 作为产物：
  描述：

  N-Boc-O-苄基-D-丝氨酸 、 C.I.酸性橙108 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 tert-butyl N-[(2R)-1-(2-hydroxyethylamino)-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
  参考文献：
  名称：

  Discovery of a Tetrazole-Based Growth Hormone Secretagogue:  4-(Hydroxybutyl)carbamic Acid 2-{5-[1-(2-Amino-2-methylpropionylamino)-2- benzyloxyethyl]tetrazol-1-yl}ethyl Ester (BMS-317180)

  摘要：

  A tetrazole-based peptidomimetic 2 (BMS-317180) was discovered as a human growth hormone secretagogue (GHS). Compound 2 is a potent, novel, orally effective GHS that shows an excellent safety profile in preclinical studies. The compound was advanced into clinical development.

  DOI：

  10.1021/jm7010595

文献信息

• Process for the preparation of tetrazol-derived compounds as growth hormone secretagogues
  申请人：Schwinden D. Mark

  公开号：US20050096466A1

  公开（公告）日：2005-05-05

  A process for the preparation of tetrazole-derived compounds useful as growth hormone secretagogues is described.

  描述了一种制备四唑衍生化合物的方法，这些化合物可用作生长激素分泌素。
• 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.
• Discovery of a Tetrazole-Based Growth Hormone Secretagogue:  4-(Hydroxybutyl)carbamic Acid 2-{5-[1-(2-Amino-2-methylpropionylamino)-2- benzyloxyethyl]tetrazol-1-yl}ethyl Ester (BMS-317180)
  作者：Jun Li、Stephanie Y. Chen、James J. Li、Haixia Wang、Andres S. Hernandez、Shiwei Tao、Christa M. Musial、Fucheng Qu、Stephen Swartz、Sam T. Chao、Neil Flynn、Brian J. Murphy、Dorothy A. Slusarchyk、Ramakrishna Seethala、Mujing Yan、Paul Sleph、Gary Grover、Mark A. Smith、Blake Beehler、Leah Giupponi、Kenneth E. Dickinson、Hongjian Zhang、William G. Humphreys、Bharat P. Patel、Mark Schwinden、Terry Stouch、Peter T. W. Cheng、Scott A. Biller、William R. Ewing、David Gordon、Jeffrey A. Robl、Joseph A. Tino

  DOI：10.1021/jm7010595

  日期：2007.11.1

  A tetrazole-based peptidomimetic 2 (BMS-317180) was discovered as a human growth hormone secretagogue (GHS). Compound 2 is a potent, novel, orally effective GHS that shows an excellent safety profile in preclinical studies. The compound was advanced into clinical development.