(4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one | 172096-94-5

• 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: (4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one
• 英文别名: (4S)-N-Boc-4-methyl-1,3-oxazolidin-5-one；(4S)-N-tert-butoxycarbonyl-4-methyl-5-oxazolidinone；tert-butyl (4S)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 172096-94-5
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: WVXNWBIDSHYNAN-LURJTMIESA-N

物化性质

• 熔点：
  64-67 °C
• 沸点：
  318.2±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (4S)-5-hydroxy-4-methyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  羧酸衍生物的Stanna-Brook重排。综合效用和机理研究。

  摘要：

  [反应：见正文] R（3）SnLi与羧酸衍生物的反应是通过一种新型的非常快的stanna-Brook重排反应进行的，该反应产生α-烷氧基有机锂化合物作为中间体。这些反应的结果取决于羧基衍生物的性质。R（3）SnLi与酯衍生物的反应通过新颖的CC键形成反应产生偶联产物。提供了详细反应机理的实验证据。

  DOI：

  10.1021/ol049826m
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 在 对甲苯磺酸一水合物 、 paraformaldehyde 作用下， 以 甲苯 为溶剂， 以71%的产率得到(4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one
  参考文献：
  名称：

  EP1340743

  摘要：

  公开号：

文献信息

• A Novel Synthesis of Oxazolidin-5-one Under Basic Condition
  作者：Sukhen Karmakar、Debendra K. Mohapatra

  DOI：10.1055/s-2001-16035

  日期：——

  A simple and practical synthesis of oxazolidin-5-one is described under basic condition.

  在基本条件下，描述了简单实用的5-氧氮杂环-2-酮合成方法。
• A practical approach for the optically pure N-Methyl-α-amino acids
  作者：G.Vidyasagar Reddy、G.Venkat Rao、D.S. Iyengar

  DOI：10.1016/s0040-4039(98)00111-7

  日期：1998.4

  A new practical synthesis of N-Methyl-α-amino acids by racemization free methodology has been developed. The method involves the reductive cleavage of N-protected oxazolidinones using hydrogen in the presence of to give the title compounds in quantitative yields.

  通过无消旋方法开发了一种新的实用的N-甲基-α-氨基酸合成方法。该方法包括在氢气存在下，用氢对N-保护的恶唑烷酮进行还原性裂解，以定量收率得到标题化合物。
• Optically active amine derivative and method of synthesis
  申请人：——

  公开号：US20040030144A1

  公开（公告）日：2004-02-12

  A readily available and inexpensive natural &agr;-amino acid is converted into a compound represented by formula (1), which is then reacted with an organometallic reagent represented by formula (2) to give an optically active 5-hydroxyoxazolidine represented by formula (3), which is then treated with an acid to provide an optically active aminoketone represented by formula (4). The product is then converted into an optically active aminoalcohol represented by formula (5) or (6) by, for example reduction. 1 The above process can provide an optically active aminoalcohol represented by formula (5) or (6) useful as a production intermediate for a medicine or pesticide from a readily available and inexpensive natural &agr;-amino acid as a starting material stereoselectively and stably with a higher optical purity and a lower cost without racemization. This invention can also provide an optically active 5-hydroxyoxazolidine represented by formula (3) and an aminoketone represented by formula (4) as important intermediates for production of the above product as well as preparation processes therefor.

  一种易得且廉价的天然α-氨基酸被转化为式（1）所表示的化合物，然后与式（2）所表示的有机金属试剂反应，得到式（3）所表示的光学活性5-羟基噁唑烷，然后用酸处理，得到式（4）所表示的光学活性氨基酮。然后，通过还原等方法将产物转化为式（5）或（6）所表示的光学活性氨基醇。以上过程可以从易得且廉价的天然α-氨基酸开始，具有高光学纯度和低成本的立体选择性和稳定性，提供用作药物或农药生产中间体的光学活性氨基醇（式（5）或（6））。本发明还可以提供式（3）所表示的光学活性5-羟基噁唑烷和式（4）所表示的氨基酮，作为上述产品生产的重要中间体以及其制备过程。
• Perfluoralkyl substituted metallo-beta-lactamase inhibitors
  申请人：Isis Innovation Limited

  公开号：US06043278A1

  公开（公告）日：2000-03-28

  The invention concerns perfluoro-lower-alkyl derivatives of amino acids. A new synthetic route is provided for preparing .alpha.-aminotrifluoromethylketones, by converting .alpha.-amino acids to oxazolidin-5-ones which are then reacted with Ruppert's Reagent. Fluorinated derivatives of amino acids and peptides are shown to have a new property of inhibiting or inactivating metallo-.beta.-lactamase enzymes, and are thus valuable components of antibacterial formulations. Certain of the trifluoromethyl derivatives of amino acids are new compounds per se.

  本发明涉及氨基酸的全氟较低烷基衍生物。提供了一种新的合成路线，用于制备α-氨基三氟甲基酮，通过将α-氨基酸转化为噁唑烷-5-酮，然后与鲁珀特试剂反应。显示氟化氨基酸和肽的衍生物具有抑制或失活金属β-内酰胺酶酶的新属性，因此是抗菌制剂中有价值的组分。某些氨基酸的三氟甲基衍生物是新的化合物本身。
• Optically active amine derivatives and preparation process therefor
  申请人：Mitsui Chemicals, Inc.

  公开号：US07026515B2

  公开（公告）日：2006-04-11

  A readily available and inexpensive natural α-amino acid is converted into a compound represented by formula (1), which is then reacted with an organometallic reagent represented by formula (2) to give an optically active 5-hydroxyoxazolidine represented by formula (3), which is then treated with an acid to provide an optically active aminoketone represented by formula (4). The product is then converted into an optically active aminoalcohol represented by formula (5) or (6) by, for example reduction.

  一种易得且廉价的天然α-氨基酸被转化为式（1）所代表的化合物，然后与式（2）所代表的有机金属试剂反应，得到式（3）所代表的光学活性5-羟基噁唑啉，然后用酸处理，得到式（4）所代表的光学活性氨基酮。然后，通过还原等方法将产物转化为式（5）或（6）所代表的光学活性氨基醇。