methyl 2-(chloromethyl)-4,5-dihydro-1,3-oxazole-4-carboxylate | 321371-33-9

• 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: methyl 2-(chloromethyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
• 英文别名: Methyl2-(chloromethyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 321371-33-9
• 化学式: C₆H₈ClNO₃
• 分子量: 177.587
• InChiKey: DHPURWFSZKRPEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(chloromethyl)-4,5-dihydro-1,3-oxazole-4-carboxylate 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 2-甲基恶唑-4-甲醛
  参考文献：
  名称：

  Large-Scale Preparation of 2-Methyloxazole-4-carboxaldehyde

  摘要：

  The large-scale preparation of 2-methyloxazole-4-carboxaldehyde presents a significant challenge due to the physical characteristics of the molecule. A method for the preparation of 10-kg batches of 2-methyloxazole-4-carboxaldehyde is described. The key reaction is the reduction of the corresponding N-methoxy-N-methyl amide using lithium aluminium hydride, followed by workup and isolation by crystallization.

  DOI：

  10.1021/op700198s
• 作为产物：
  描述：

  DL-丝氨酸甲酯盐酸盐 、 氯乙腈 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 methyl 2-(chloromethyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Large-Scale Preparation of 2-Methyloxazole-4-carboxaldehyde

  摘要：

  The large-scale preparation of 2-methyloxazole-4-carboxaldehyde presents a significant challenge due to the physical characteristics of the molecule. A method for the preparation of 10-kg batches of 2-methyloxazole-4-carboxaldehyde is described. The key reaction is the reduction of the corresponding N-methoxy-N-methyl amide using lithium aluminium hydride, followed by workup and isolation by crystallization.

  DOI：

  10.1021/op700198s

文献信息

• An Efficient, Practical Approach to the Synthesis of 2,4-Disubstituted Thiazoles and Oxazoles:  Application to the Synthesis of GW475151
  作者：Stephen A. Hermitage、Kevin S. Cardwell、Tim Chapman、Jason W. B. Cooke、Rebecca Newton

  DOI：10.1021/op000086g

  日期：2001.1.1

  A new method for the synthesis of 2,4-disubstituted oxazoles and thiazoles and 2,4,5-trisubstituted oxazoles from readily available starting materials is described. The methodology has been applied on multigram scale and involves transfer of oxidation state through a molecular framework. In particular the oxazole-containing amino acid fragment of the 5,5-trans-fused lactam GW475151, 1, has been prepared

  描述了一种从容易获得的起始材料合成 2,4-二取代恶唑和噻唑以及 2,4,5-三取代恶唑的新方法。该方法已应用于数克规模，并涉及通过分子框架转移氧化态。特别是 5,5-反式稠合内酰胺 GW475151, 1 的含恶唑氨基酸片段已以优异的产率和纯度制备。
• Calpain modulators and therapeutic uses thereof
  申请人：Blade Therapeutics, Inc.

  公开号：US10934261B2

  公开（公告）日：2021-03-02

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文公开了小分子钙蛋白酶调节剂组合物、药物组合物及其用途和制备方法。
• [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2018064119A8

  公开（公告）日：2019-04-25
• 2-Amino-6-Methyl-4,4a,5,6-Tetrahydropyrano[3,4-d][1,3]Thiazin-8a(8H)-yl-1,3-Thiazol-4-yl Amides
  申请人：Pfizer Inc.

  公开号：US20170151252A1

  公开（公告）日：2017-06-01

  The present invention is directed to compounds, tautomers and pharmaceutically acceptable salts of the compounds which are disclosed, wherein the compounds have the structure of Formula I, and the variable R 1 is as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.