tert-butyl 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-ylcarbamate | 339185-93-2

• 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 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-ylcarbamate
• 英文别名: [1-(N-methoxy-N-methylcarbamoyl)-3-methylbutyl]carbamic acid tert-butyl ester；tert-butyl N-{1-[methoxy(methyl)carbamoyl]-3-methylbutyl}carbamate；tert-butyl N-[1-[methoxy(methyl)amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 339185-93-2
• 化学式: C₁₃H₂₆N₂O₄
• mdl: MFCD24390154
• 分子量: 274.36
• InChiKey: IKRXSZUARJIXLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-ylcarbamate 在 lithium aluminium tetrahydride 作用下， 以90%的产率得到(1-Formyl-3-methylbutyl)carbamic acid,1,1-dimethylethyl ester
  参考文献：
  名称：

  使用2-三甲基甲硅烷基乙基三苯甲基膦烷对氨基醛进行立体选择性乙烯基化

  摘要：

  2-三甲基甲硅烷基乙基三苯苯基膦烷与α-氨基醛立体选择性地反应，得到羰基乙烯基化的Cram螯合控制产物。通过该反应获得的烯属1,2-氨基醇是制备肽类似物的重要中间体，并且被用于制备N-Boc-他汀。

  DOI：

  10.1016/s0040-4039(00)93602-5
• 作为产物：
  描述：

  ethyl N-tert-butyloxycarbonyl-2-amino-4-methyl-pentanoate 在 N-甲基吗啉 、 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-ylcarbamate
  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

文献信息

• Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β³-Amino Acid Analogues
  作者：Basker Rajagopal、Ying-Yu Chen、Chun-Chi Chen、Xuan-Yu Liu、Huei-Ren Wang、Po-Chiao Lin

  DOI：10.1021/jo402670d

  日期：2014.2.7

  A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80–95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety

  已经成功地开发了铜（I）催化炔酮胺中间体从炔丙基酰胺合成取代的二氢嘧啶-4-酮。合成得到良好的分离产率（80-95％）。室温下温和的反应条件可使反应在数小时内完成，而无需改变立体化学。另外，通过涉及多种反应性亲核试剂，将得到的被取代的二氢嘧啶-4-酮被优雅转化成相应的β-和β 3 -氨基酸的类似物。
• [EN] PROCESS FOR THE PREPARATION OF (2S)-N-((S)-1-((S)-4-METHYL-1-((R)-2-METHYL OXIRAN-2-YL)-1-OXOPENTAN-2-YLCARBAMOYL)-2-PHENYLETHYL)-2-((S)-2-(2-MORPHOLINO ACETAMIDO)-4-PHENYLBUTANAMIDO)-4-METHYLPENTANAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (2S)-N-((S)-1-((S)-4-MÉTHYL-1-((R)-2-MÉTHYL OXIRAN-2-YL)-1-OXOPENTAN-2-YLCARBAMOYL)-2-PHÉNYLÉTHYL)-2-((S)-2-(2-MORPHOLINO ACÉTAMIDO)-4-PHÉNYLBUTANAMIDO)-4-MÉTHYLPENTANAMIDE
  申请人：MSN LABORATORIES PRIVATE LTD

  公开号：WO2016170544A1

  公开（公告）日：2016-10-27

  The present invention relates to process for the preparation of (2S)-N-((S)-l -((S)-4-methyl-1 -((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylcarbamoyl)-2-phenylethyl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)-4 -methylpentanamide represented by the following structural formula-1.

  本发明涉及一种制备(2S)-N-((S)-l -((S)-4-甲基-1-((R)-2-甲氧基环氧丙基-1-氧代戊基氨基)-2-苯乙基)-2-((S)-2-(2-吗啉基乙酰氨基)-4-苯基丁酰氨基)-4-甲基戊酰胺的方法，其结构式如下所示-1。
• Tosylhydrazide-Promoted Diastereoselective Intramolecular 1,3-Dipolar Cycloadditions: Synthesis of Tetrahydropyrrolo[3,4-<i>c</i>]pyrazoles
  作者：Raquel Barroso、Maria Escribano、Maria-Paz Cabal、Carlos Valdés

  DOI：10.1002/ejoc.201301587

  日期：2014.3

  α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation

  描述了通过分子内 1,3-偶极环加成非对映选择性合成四氢吡咯并 [3,4-c] 吡唑。合成路线的起始原料是 N-Boc 保护的 α-氨基酸，首先通过常规方法将其转化为 N-烯丙基-α-氨基酮。然后，包括从酮形成甲苯磺酰腙、腙的碱诱导分解和生成的重氮化合物的分子内 1,3-偶极环加成的一锅序列产生具有总非对映选择性和高的双环系统保持对映体纯度。然而，使用 α-氨基醛的类似方法缺乏立体选择性。已经进行了 DFT 计算建模以解释两种类型系统的不同行为。
• [EN] INHIBITORS OF HISTONE DEMETHYLASES<br/>[FR] INHIBITEURS D'HISTONES DÉMÉTHYLASES
  申请人：EPITHERAPEUTICS APS

  公开号：WO2015153498A1

  公开（公告）日：2015-10-08

  Compounds of the form in which Q is selected from -COOH -CH=NR12, -W, -CH2NHR13, -CH=0 and -CH(OR17)2 capable of modulating the activity of histone demethylases (HDMEs), which are useful for prevention and/or treatment of diseases in which genomic dysregulation is involved in the pathogenesis, such as e.g. cancer and formulations and methods of use of such compounds.

  Q被选择为-COOH、-CH=NR12、-W、-CH2NHR13、-CH=0和-CH(OR17)2形式的化合物，能够调节组蛋白去甲基化酶(HDMEs)的活性，这些化合物对于预防和/或治疗基因组失调参与病因学的疾病，如癌症等，以及这些化合物的配方和使用方法是有用的。
• Nitrile compounds useful as reversible inhibitors of &num;9 cathepsin 5
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US06395897B1

  公开（公告）日：2002-05-28

  Disclosed are cathepsin S reversible inhibitory compounds of the formulas (I),(Ia) and (II),(IIa) as defined herein. The compounds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds.

  本文披露了如下公式(I)、(Ia)和(II)、(IIa)所定义的蛋白酶S可逆抑制化合物。这些化合物可用于治疗自身免疫性疾病。同时还披露了制备这些新型化合物的方法。