ethyl 3-(3-((t-butoxycarbonyl)amino)propanamido)propanoate | 173406-16-1

• 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: ethyl 3-(3-((t-butoxycarbonyl)amino)propanamido)propanoate
• 英文别名: Boc-di-β-Ala-OEt；Ethyl 3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoate；ethyl 3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoate
• CAS: 173406-16-1
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: ZLVLCKUFEZKIPB-UHFFFAOYSA-N

物化性质

• 沸点：
  474.7±30.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3-((t-butoxycarbonyl)amino)propanamido)propanoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以35 mg的产率得到Boc-β-Ala2-OH
  参考文献：
  名称：

  Development of a Clinically Viable Heroin Vaccine

  摘要：

  Heroin is a highly abused opioid and incurs a significant detriment to society worldwide. In an effort to expand the limited pharmacotherapy options for opioid use disorders, a heroin conjugate vaccine was developed through comprehensive evaluation of hapten structure, carrier protein, adjuvant and dosing. Immunization of mice with an optimized heroin-tetanus toxoid (TT) conjugate formulated with adjuvants alum and CpG oligodeoxynucleotide (ODN) generated heroin immunoantagonism, reducing heroin potency by >15-fold. Moreover, the vaccine effects proved to be durable, persisting for over eight months. The lead vaccine was effective in rhesus monkeys, generating significant and sustained antidrug IgG titers in each subject. Characterization of both mouse and monkey antiheroin antibodies by surface plasmon resonance (SPR) revealed low nanomolar antiserum affinity for the key heroin metabolite, 6-acetylmorphine (6AM), with minimal cross reactivity to clinically used opioids. Following a series of heroin challenges over six months in vaccinated monkeys, drug-sequestering antibodies caused marked attenuation of heroin potency (>4-fold) in a schedule-controlled responding (SCR) behavioral assay. Overall, these preclinical results provide an empirical foundation supporting the further evaluation and potential clinical utility of an effective heroin vaccine in treating opioid use disorders.

  DOI：

  10.1021/jacs.7b03334
• 作为产物：
  描述：

  3-氨基丙酸乙酯 、 Boc-beta-丙氨酸 在 2-碘-5-甲氧基苯硼酸 作用下， 以 甲苯 为溶剂， 反应 48.17h， 以60%的产率得到ethyl 3-(3-((t-butoxycarbonyl)amino)propanamido)propanoate
  参考文献：
  名称：

  MIBA催化的直接酰胺化的多克级电子因子降低程序及其在α和β氨基酸偶联中的应用

  摘要：

  由于酰胺和肽作为药物和日用化学品的组成部分的重要性，直接和原子经济的酰胺化方法的开发是高度优先的。本文介绍...

  DOI：

  10.1039/c5gc00659g

文献信息

• [EN] BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS<br/>[FR] CATALYSEURS À BASE D'ACIDE BORONIQUE ET PROCÉDÉS D'UTILISATION ASSOCIÉS POUR L'ACTIVATION ET LA TRANSFORMATION D'ACIDES CARBOXYLIQUES
  申请人：UNIV ALBERTA

  公开号：WO2012109749A1

  公开（公告）日：2012-08-23

  The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:

  本申请提供了用于活化羧酸进行有机反应的方法和催化剂。具体而言，揭示了用于直接亲核加成反应的方法，例如与胺的酰胺化反应，环加成和共轭加成，使用式I、II或III的硼酸催化剂：还包括式IV、V和III的新型硼酸催化剂：
• A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids
  作者：Solmaz Fatemi、Nicolas Gernigon、Dennis G. Hall

  DOI：10.1039/c5gc00659g

  日期：——

  The development of direct and atom-economical amidation methods is of high priority because of the importance of amides and peptides as components of pharmaceuticals and commodity chemicals. This article describes...

  由于酰胺和肽作为药物和日用化学品的组成部分的重要性，直接和原子经济的酰胺化方法的开发是高度优先的。本文介绍...
• Boronic Acid Catalysts and Methods of Use Thereof for Activation and Transformation of Carboxylic Acids
  申请人：Hall Dennis

  公开号：US20140142322A1

  公开（公告）日：2014-05-22

  The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:

  本申请提供了激活羧酸进行有机反应的方法和催化剂。具体而言，揭示了使用式I、II或III的硼酸催化剂进行直接亲核加成反应的方法，例如与胺的酰胺化反应、环加成反应和共轭加成反应。还包括式IV、V和III的新型硼酸催化剂。
• Development of a Clinically Viable Heroin Vaccine
  作者：Paul T. Bremer、Joel E. Schlosburg、Matthew L. Banks、Floyd. F. Steele、Bin Zhou、Justin L. Poklis、Kim D. Janda

  DOI：10.1021/jacs.7b03334

  日期：2017.6.28

  Heroin is a highly abused opioid and incurs a significant detriment to society worldwide. In an effort to expand the limited pharmacotherapy options for opioid use disorders, a heroin conjugate vaccine was developed through comprehensive evaluation of hapten structure, carrier protein, adjuvant and dosing. Immunization of mice with an optimized heroin-tetanus toxoid (TT) conjugate formulated with adjuvants alum and CpG oligodeoxynucleotide (ODN) generated heroin immunoantagonism, reducing heroin potency by >15-fold. Moreover, the vaccine effects proved to be durable, persisting for over eight months. The lead vaccine was effective in rhesus monkeys, generating significant and sustained antidrug IgG titers in each subject. Characterization of both mouse and monkey antiheroin antibodies by surface plasmon resonance (SPR) revealed low nanomolar antiserum affinity for the key heroin metabolite, 6-acetylmorphine (6AM), with minimal cross reactivity to clinically used opioids. Following a series of heroin challenges over six months in vaccinated monkeys, drug-sequestering antibodies caused marked attenuation of heroin potency (>4-fold) in a schedule-controlled responding (SCR) behavioral assay. Overall, these preclinical results provide an empirical foundation supporting the further evaluation and potential clinical utility of an effective heroin vaccine in treating opioid use disorders.