(S)-methyl 2-(1H-imidazole-1-carboxamido)-3-methylbutanoate | 93605-47-1

• 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: (S)-methyl 2-(1H-imidazole-1-carboxamido)-3-methylbutanoate
• 英文别名: Imi-Val-OMe；2-[(Imidazole-1-carbonyl)-amino]-3-methyl-butyric acid methyl ester；methyl (2S)-2-(imidazole-1-carbonylamino)-3-methylbutanoate
• CAS: 93605-47-1
• 化学式: C₁₀H₁₅N₃O₃
• 分子量: 225.247
• InChiKey: FIESZNOTTXYIRS-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(1H-imidazole-1-carboxamido)-3-methylbutanoate 在 三乙胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.5h， 生成 (8S,9S,13S)-methyl 8-(2-acetoxyethyl)-9-(((S)-1-tert-butoxy-4-methy l-1-oxopentan-2-yl)carbamoyl)-6-((tert-butoxycarbonyl)amino)-13-isopropyl-2,2-dimethyl-4,11-dioxo-3-oxa-5,7,10,12-tetraazatetradec-5-en-14-oate
  参考文献：
  名称：

  Synthesis of Ureidomuraymycidine Derivatives for Structure– Activity Relationship Studies of Muraymycins

  摘要：

  One of the key constituents of the muraymycins is the 6-membered cyclic guanidine, (2S,3S)-muraymycidine (or epi-capreomycidine). In order to diversify the structure of the oligopeptide moiety of the muraymycins for thorough structure activity relationship studies, we have developed a highly stereoselective synthesis of ureidomuraymycidine derivatives with the lactone 4a.

  DOI：

  10.1021/jo300205b
• 作为产物：
  描述：

  L-缬氨酸盐酸盐 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到(S)-methyl 2-(1H-imidazole-1-carboxamido)-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of Ureidomuraymycidine Derivatives for Structure– Activity Relationship Studies of Muraymycins

  摘要：

  One of the key constituents of the muraymycins is the 6-membered cyclic guanidine, (2S,3S)-muraymycidine (or epi-capreomycidine). In order to diversify the structure of the oligopeptide moiety of the muraymycins for thorough structure activity relationship studies, we have developed a highly stereoselective synthesis of ureidomuraymycidine derivatives with the lactone 4a.

  DOI：

  10.1021/jo300205b

文献信息

• Inverse Peptide Synthesis via Activated α-Aminoesters
  作者：Jean-Simon Suppo、Gilles Subra、Matthieu Bergès、Renata Marcia de Figueiredo、Jean-Marc Campagne

  DOI：10.1002/anie.201402147

  日期：2014.5.19

  procedure for peptide‐bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated α‐aminoesters. The method provides a straightforward entry to dipeptides and was effective when a sensitive cysteine residue was used, as no epimerization was detected in this case. The applicability of this method to iterative peptide synthesis

  报道了一种温和，实用和简单的肽键形成步骤。除了活化羧酸官能团之外，该反应还涉及前所未有的活化α-氨基酯的使用。该方法提供了直接进入二肽的方法，并且在使用敏感的半胱氨酸残基时有效，因为在这种情况下未检测到差向异构。通过在具有挑战性的N→C方向上合成模型四肽，说明了该方法在迭代肽合成中的适用性。
• N,N′-Carbonyldiimidazole-Mediated DBU-Catalyzed One-Pot Synthesis of Urea-Tethered Glycosyl Amino Acids and Glycoconjugates
  作者：V. Sureshbabu

  DOI：10.1055/s-0030-1259958

  日期：2011.5

  An efficient, mild, simple, and alternative one-pot protocol for the synthesis of urea-tethered glycosyl amino acids mediated by N,N′-carbonyldiimidazole employing DBU as a catalyst is described. This protocol is also extended for the synthesis of urea-tethered disaccharides and oligosaccharides.

  报道了一种高效、温和、简单且可替代的一锅法合成脲键连接的糖基氨基酸的协议，该协议通过N,N'-碳酰二咪唑介导，采用DBU作为催化剂。该协议还可扩展用于合成脲键连接的双糖和低聚糖。
• Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI-<i>N</i>-Protected α-Aminoesters
  作者：Renata Marcia de Figueiredo、Jean-Simon Suppo、Camille Midrier、Jean-Marc Campagne

  DOI：10.1002/adsc.201700034

  日期：2017.6.6

  The synthesis of dipeptides through a sequential one‐pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI‐protected α‐amino esters (CDI, e.g. N,N′‐carbonyldiimidazole). In addition of being a highly atom‐economical process, the couplings take place under very mild and neutral conditions without adding

  描述了通过顺序的一锅法从市售受保护的氨基酸合成二肽的方法。转化依赖于使用原位生成的瞬时CDI保护的α-氨基酯（CDI，例如N，N'-羰基二咪唑）。除了是高度原子经济的过程外，偶联还可以在非常温和和中性的条件下进行，而无需在反应介质中添加碱。该方案为二肽衍生物的制备提供了一条简洁且成本较低的途径（12个实例，收率高达87％），并且与常用的N-氨基甲酸酯保护基团兼容。此外，即使使用敏感的Boc-Cys（Bn）-OH，也未检测到差向异构。
• Amino acid derived latent isocyanates: irreversible inactivation of porcine pancreatic elastase and human leukocyte elastase
  作者：William C. Groutas、William R. Abrams、Michael C. Theodorakis、Annette M. Kasper、Steven A. Rude、Robert C. Badger、Timothy D. Ocain、Kevin E. Miller、Min K. Moi

  DOI：10.1021/jm00380a010

  日期：1985.2

  were found to inhibit irreversibly both enzymes. Compound 10 was found to be a specific and selective inhibitor of human leukocyte elastase. In contrast to these, inhibitors derived from glycine methyl ester 1, D-valine methyl ester 4, and D-norvaline methyl ester 6 were found to be inactive. The results of the present study show that latent isocyanates derived from appropriate amino acids can serve as

  已经合成了几种氨基酸衍生的偶氮内酯（I），并研究了它们对人白细胞弹性蛋白酶和猪胰弹性蛋白酶的抑制活性。发现抑制活性取决于前体氨基酸酯的性质。因此，发现衍生自L-缬氨酸甲酯3，L-正缬氨酸甲酯5，DL-正亮氨酸甲酯9和L-甲硫氨酸甲酯10的化合物不可逆地抑制两种酶。发现化合物10是人白细胞弹性蛋白酶的特异性和选择性抑制剂。与这些相反，发现衍生自甘氨酸甲酯1，D-缬氨酸甲酯4和D-去甲缬氨酸甲酯6的抑制剂是无活性的。
• Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives
  作者：Laure Konnert、Lori Gonnet、Ivan Halasz、Jean-Simon Suppo、Renata Marcia de Figueiredo、Jean-Marc Campagne、Fredéric Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.1021/acs.joc.6b01832

  日期：2016.10.21

  5-Substituted-3-(alkoxycarbonyl)alkyl-hydantoin derivatives were prepared by mechanochemistry from amino esters or dipeptides, via a 1,1′-carbonyldiimidazole-mediated one-pot/two-step cyclization reaction involving amino acid unsymmetrical urea A and carboxy-imidazolyl-dipeptide ester B intermediates. Comparative experiments in solution were also performed. The successful preparation of an antibacterial agent precursor

  通过1,1'-羰基二咪唑介导的涉及氨基酸不对称尿素A和羧基的一锅/两步环化反应，通过机械化学方法从氨基酯或二肽中制备5-取代的3-（烷氧基羰基）烷基-乙内酰脲衍生物-咪唑基-二肽酯B中间体。还进行了溶液中的对比实验。还研究了抗菌剂前体的成功制备。