(4S,5R)-4-苄基-2-恶唑烷酮-5-羧酸甲酯 | 147976-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (4S,5R)-4-苄基-2-恶唑烷酮-5-羧酸甲酯
• 英文名称: (4S,5R)-4-benzyl-5-[(methoxy)carbonyl]-1,3-oxazolidin-2-one
• 英文别名: (4S,5R)-4-benzyl-2-oxazolidinone-5-carboxylic acid methyl ester；methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylate；methyl (4S,5R)-4-benzyl-2-oxo-1,3-oxazolidine-5-carboxylate
• CAS: 147976-17-8
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: ZQRVBTPPEJVLAQ-VHSXEESVSA-N

物化性质

• 沸点：
  442.6±34.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (4S,5R)-4-苄基-2-恶唑烷酮-5-羧酸甲酯 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 60.0h， 以82%的产率得到(2R,3S)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND

  摘要：

  本发明提供了一种从在β-位置具有离去基团的N-烷氧羰基乙基胺化合物出发，制备具有β-位置碳上反转立体构型的β-羟基乙基胺化合物的噁唑烷酮衍生物的方法，该方法包括在过程中引入与水接触并在酸性至中性条件下加热处理的步骤。此外，本发明提供了一种从在β-位置具有离去基团的N-烷氧羰基乙基胺化合物出发，制备具有β-位置碳上反转立体构型的β-羟基乙基胺化合物的方法，该方法包括将上述制备的噁唑烷酮衍生物在与水接触的步骤中在碱性条件下处理。

  公开号：

  EP1403257A1
• 作为产物：
  描述：

  1-(S)-cyano-2(S)-(N-tert-butoxycarbonylamino)-3-phenylpropyl benzoate 在 氯化亚砜 、 三乙胺 作用下， 生成 (4S,5R)-4-苄基-2-恶唑烷酮-5-羧酸甲酯
  参考文献：
  名称：

  A concise synthesis of aza-dipeptide isosteres

  摘要：

  Aza-dipeptide isosteres as potent HIV-protease inhibitors containing a (hydroxyethyl)-hydrazine moiety are synthesised in >98% diastereomeric and enantiomeric purity starting from (L)-phenylalanine aldehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00897-1

文献信息

• O−N Intramolecular Alkoxycarbonyl Migration of Typical Protective Groups in Hydroxyamino Acids
  作者：Mariusz Skwarczynski、Youhei Sohma、Mayo Noguchi、Tooru Kimura、Yoshio Hayashi、Yoshiaki Kiso

  DOI：10.1021/jo0525579

  日期：2006.3.1

  O−N Intramolecular alkoxycarbonyl (carbonate−carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.

  发现O-N分子内烷氧基羰基（碳酸盐-氨基甲酸酯）迁移是在温和的碱性水溶液条件下发生的羟氨基酸的常见反应，没有副产物的形成。碳酸盐保护基团迁移以高效和高纯度地产生羟基氨基酸的氨基保护的氨基甲酸酯衍生物。
• PROCESS FOR PRODUCING 3-AMINO-2-HYDROXYPROPIONIC ACID DERIVATIVES
  申请人：MURAO Hiroshi

  公开号：US20060135784A1

  公开（公告）日：2006-06-22

  The present invention provides a process for preparing 3-amino-2-hydroxypropionic acid derivatives (1) which does not use dangerous reagents, is economically advantageous, and is suitable for an industrial production, which process comprises: treating N-protected-3-amino-2-hydroxypropionic acid derivatives (2) having a steric configuration at 2-position carbon reverse to that of derivatives (1) with a leaving group-introducing agent to convert into N-protected-3-aminopropionic acid derivatives (3), then treating the derivatives with a basic substance to convert into substituted-3-amino-2-hydroxypropionic acid derivatives (4) having an inverted steric configuration at 2-position carbon, and then converting the derivatives into 3-amino-2-hydroxypropionic acid derivatives (1).

  本发明提供了一种制备3-氨基-2-羟基丙酸衍生物（1）的过程，该过程不使用危险试剂，经济优势明显，适用于工业生产。该过程包括：用离去基引入试剂处理在2位碳的立体构型与衍生物（1）相反的N-保护的3-氨基-2-羟基丙酸衍生物（2），转化为N-保护的3-氨基丙酸衍生物（3），然后用碱性物质处理衍生物，转化为在2位碳具有反向立体构型的取代3-氨基-2-羟基丙酸衍生物（4），最后将衍生物转化为3-氨基-2-羟基丙酸衍生物（1）。
• Process for the manufacture of (4,5)-trans-oxazolidines
  申请人：Hoffmann-La Roche Inc.

  公开号：US05670653A1

  公开（公告）日：1997-09-23

  Compounds containing a (4,5)-cis-2-oxo-oxazolidine ring are isomerized to the corresponding (4,5)-trans-2-oxo-oxazolidine by treating the cis compound with a strong base.

  含有(4,5)-顺式-2-氧代噁唑啉环的化合物可以通过使用强碱处理顺式化合物，使其异构化为相应的(4,5)-反式-2-氧代噁唑啉。
• Process for producing oxazolidinone derivative of beta-hydroxyethylamine compound and for producing beta-hydroxyethlamine compound
  申请人：——

  公开号：US20040181074A1

  公开（公告）日：2004-09-16

  The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the &bgr;-position to prepare oxazolidinone derivatives of &bgr;-hydroxyethylamine compounds having an inverted steric configuration at the &bgr;-position carbon, which comprises introducing a step of treating in contact with water with heating under acidic to neutral conditions into the process. Also, the present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the &bgr;-position to prepare &bgr;-hydroxyethylamine compounds having an inverted steric configuration at the &bgr;-position carbon, which comprises subjecting the oxazolidinone derivatives prepared as described above to a step of treating in contact with water under basic conditions.

  本发明提供了一种从&bgr;-位具有离去基团的N-烷氧羰基-乙胺化合物开始制备&bgr;-位碳具有倒立体构型的&bgr;-羟乙基胺化合物的噁唑烷酮衍生物的工艺，该工艺包括在酸性至中性条件下引入与水接触并加热处理的步骤。此外，本发明还提供了一种从在&bgr;-位上具有离去基团的N-烷氧基羰基-乙胺化合物开始制备在&bgr;-位碳上具有倒立体构型的&bgr;-羟乙基胺化合物的工艺，该工艺包括将如上所述制备的噁唑烷酮衍生物在碱性条件下与水接触处理的步骤。
• Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active <i>syn</i>-β-Amino-α-hydroxy Esters
  作者：Karsten Juhl、Karl Anker Jørgensen

  DOI：10.1021/ja0175486

  日期：2002.3.1

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.