ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate | 756498-96-1

• 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 N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate
• 英文别名: Ethyl 2-[(tert-butoxycarbonyl)amino]-4-methylpentanoate；ethyl 4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 756498-96-1
• 化学式: C₁₃H₂₅NO₄
• mdl: MFCD24390100
• 分子量: 259.346
• InChiKey: XBFXYJDHVNLXAC-UHFFFAOYSA-N

物化性质

• 沸点：
  338.5±25.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate 在 N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 双氧水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (S)-3-Amino-(R)-2-hydroxy-5-methylhexanamide hydrochloride
  参考文献：
  名称：

  Discovery of (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]- 3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]- 6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a Selective, Potent, Orally Bioavailable Hepatitis C Virus NS3 Protease Inhibitor:  A Potential Therapeutic Agent for the Treatment of Hepatitis C Infection

  摘要：

  Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-alpha or polyethylene glycol (PEG)-interferon-alpha alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

  DOI：

  10.1021/jm060325b
• 作为产物：
  描述：

  4-甲基-2-氧代戊酸乙酯 在 三乙基硼 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate
  参考文献：
  名称：

  模仿酶促氨基转移：尝试理解和发展手性α-氨基酸的催化不对称方法。

  摘要：

  试图通过机理研究和在不对称催化与酶促反应之间架起桥梁，并发展了一种手性路易斯酸催化的伯胺催化α-酮基酯的催化和对映选择性方法的氨基化反应，作为氨基转移酶的模型。使用伯胺氮源（例如吡nitrogen胺和4-吡啶甲基胺），不同的路易斯酸可以催化α-酮基酯的半氨基转移。使用氘标记的化合物对路易斯酸催化的半反式氨基转移的机理研究表明，氘原子在α-氨基酸衍生物的多个位置上掺入，表明α-酮酯的烯醇在其中起着重要的作用。反应路径。催化对映选择性反应取决于溶剂的pKa值，因为对映选择性仅在相对于甲醇具有高pKa值的溶剂中获得。但是，较强的酸性条件通常可提供较好的收率，但对映选择性差。筛选了一系列手性路易斯酸作为对映选择性半氨基转移反应的催化剂，并获得了中等收率和高达46％ee的对映选择性。

  DOI：

  10.1039/b404381b

文献信息

• Aryl Substituted Indoles and Their Use as Blockers of Sodium Channels
  申请人：Kyle Donald J.

  公开号：US20130296281A1

  公开（公告）日：2013-11-07

  The invention relates to aryl and heteroaryl substituted compounds of Formula (I), and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein G, R 1 , and Z 1 -Z 5 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

  本发明涉及具有式（I）的芳基和杂芳基取代化合物，以及其药学上可接受的盐、前药或溶剂化物，其中G、R1和Z1-Z5如规范中所述。本发明还涉及利用式（I）的化合物治疗对钠通道阻滞有响应的疾病。本发明的化合物特别适用于治疗疼痛。
• Aryl substituted indoles and the use thereof
  申请人：Purdue Pharma L.P.

  公开号：US10202344B2

  公开（公告）日：2019-02-12

  The invention relates to aryl and heteroaryl substituted compounds of Formula (I), and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein G, R1, and Z1-Z5 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

  本发明涉及式（I）的芳基和杂芳基取代的化合物及其药学上可接受的盐、原药或溶液，其中G、R1和Z1-Z5的定义如说明书所述。本发明还涉及使用式（I）化合物治疗对阻断钠通道有反应的疾病。本发明的化合物特别适用于治疗疼痛。
• Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids
  作者：Eleonora Agosta、Antonio Caligiuri、Paola D’Arrigo、Stefano Servi、Davide Tessaro、Renato Canevotti

  DOI：10.1016/j.tetasy.2006.07.012

  日期：2006.8

  Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-BOC L-acids and D-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of D-t-leucine, for which a practical method is currently unavailable. (c) 2006 Elsevier Ltd. All rights reserved.
• ARYL SUBSTITUTED INDOLES AND THE USE THEREOF
  申请人：Purdue Pharma L.P.

  公开号：US20160326111A1

  公开（公告）日：2016-11-10

  The invention relates to aryl and heteroaryl substituted compounds of Formula (I), and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein G, R 1 , and Z 1 -Z 5 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.
• US8486994B2
  申请人：——

  公开号：US8486994B2

  公开（公告）日：2013-07-16