(S)-3-[2-(2-methoxyphenoxy)ethyl]-5-(hydroxymethyl)oxazolidin-2-one | 947703-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-[2-(2-methoxyphenoxy)ethyl]-5-(hydroxymethyl)oxazolidin-2-one
• 英文别名: (5S)-5-(hydroxymethyl)-3-[2-(2-methoxyphenoxy)ethyl]-1,3-oxazolidin-2-one
• CAS: 947703-53-9
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: RFXCZMQQLBUMCR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-[2-(2-methoxyphenoxy)ethyl]-5-(hydroxymethyl)oxazolidin-2-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到(S)-{3-[2-(2-methoxyphenoxy)ethyl]-2-oxooxazolidin-5-yl}methyl methanesulfonate
  参考文献：
  名称：

  WO2007/97504

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-t-叔丁基缩水甘油醚 在 lithium tert-butoxide 、 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 以96%的产率得到(S)-3-[2-(2-methoxyphenoxy)ethyl]-5-(hydroxymethyl)oxazolidin-2-one
  参考文献：
  名称：

  WO2007/97504

  摘要：

  公开号：

文献信息

• Process for the preparation of highly optical pure carvedilol
  申请人：AHN-Gook Pharmaceutical Co., Ltd.

  公开号：US08101781B2

  公开（公告）日：2012-01-24

  The present invention relates to a process for the efficient preparation of highly optical pure chiral carvedilol. According to the present invention, a chiral oxazolidin-2-one or oxazolidin-2-thione having formula 2, produced from the reaction of N-protected 2-(2-methoxyphenoxy)ethylamine with a chiral glycidol derivative is used as a key intermediate for the preparation of the chiral carvedilol. Specifically, the process for the preparation of the chiral carvedilol comprises a) reacting a compound of formula 2 with a halogenation agent, a sulfonation agent or a mitsunobu reagent to activate a hydroxyl group of the compound of formula 2, followed by nucleophilic substitution reaction with 9H-4-hydroxy carbazole to produce a compound of formula 7, and b) subjecting the obtained compound of formula 7 to a deprotection reaction in a presence of an inorganic base to produce the targeted chiral carvedilol. The process of the present invention can be accomplished in a mild condition. The process neither requires any extraordinary purification procedure, nor involves decrease of optical purity. Therefore, the process of the present invention provides highly optical pure chiral carvedilol in simple and efficient manner.

  本发明涉及一种制备高光学纯手性卡维地洛的高效过程。根据本发明，将由N-保护的2-(2-甲氧基苯氧基)乙胺与手性环氧丙醇衍生物反应制备的手性噁唑烷-2-酮或噁唑烷-2-硫酮，其化学式为2，作为制备手性卡维地洛的关键中间体。具体地，制备手性卡维地洛的过程包括：a）将化合物2与卤化试剂、磺化试剂或三宅信试剂反应，以激活化合物2的羟基，然后通过亲核取代反应与9H-4-羟基咔唑反应，得到化合物7；b）在无机碱存在下，对得到的化合物7进行去保护反应，得到目标手性卡维地洛。本发明的过程可以在温和条件下完成，既不需要任何特殊的纯化步骤，也不会降低光学纯度。因此，本发明的过程以简单、高效的方式提供了高光学纯手性卡维地洛。
• PROCESS FOR THE PREPARATION OF HIGHLY OPTICAL PURE CARVEDILOL
  申请人：Kim Seong-Jin

  公开号：US20090176992A1

  公开（公告）日：2009-07-09

  The present invention relates to a process for the efficient preparation of highly optical pure chiral carvedilol. According to the present invention, a chiral oxazolidin-2-one or oxazolidin-2-thione having formula 2, produced from the reaction of N-protected 2-(2-methoxyphenoxy)ethylamine with a chiral glycidol derivative is used as a key intermediate for the preparation of the chiral carvedilol. Specifically, the process for the preparation of the chiral carvedilol comprises a) reacting a compound of formula 2 with a halogenation agent, a sulfonation agent or a mitsunobu reagent to activate a hydroxyl group of the compound of formula 2, followed by nucleophilic substitution reaction with 9H-4-hydroxy carbazole to produce a compound of formula 7, and b) subjecting the obtained compound of formula 7 to a deprotection reaction in a presence of an inorganic base to produce the targeted chiral carvedilol. The process of the present invention can be accomplished in a mild condition. The process neither requires any extraordinary purification procedure, nor involves decrease of optical purity. Therefore, the process of the present invention provides highly optical pure chiral carvedilol in simple and efficient manner.

  本发明涉及一种高效制备高度光学纯手性卡维地洛的方法。根据本发明，使用由保护的N-2-(2-甲氧基苯氧基)乙基胺与手性环氧丙醇衍生物反应生成的式2手性噁唑烷-2-酮或噁唑烷-2-硫酮作为制备手性卡维地洛的关键中间体。具体而言，制备手性卡维地洛的过程包括a)将式2化合物与卤化剂、磺化剂或三宅信试剂反应以激活式2化合物的羟基，随后与9H-4-羟基咔唑进行亲核取代反应，生成式7化合物，并b)在无机碱存在下对得到的式7化合物进行去保护反应，生成目标手性卡维地洛。本发明的过程可以在温和条件下完成，既不需要任何特殊的纯化过程，也不涉及光学纯度的降低。因此，本发明的方法以简单高效的方式提供高度光学纯的手性卡维地洛。
• US8101781B2
  申请人：——

  公开号：US8101781B2

  公开（公告）日：2012-01-24
• [EN] PROCESS FOR THE PREPARATION OF HIGHLY OPTICAL PURE CARVEDILOL<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CARVÉDILOL CHIRAL DE HAUTE PURETÉ OPTIQUE
  申请人：AHN GOOK PHARMACEUTICAL CO LTD

  公开号：WO2007097504A1

  公开（公告）日：2007-08-30

  [EN] The present invention relates to a process for the efficient preparation of highly optical pure chiral carvedilol. According to the present invention, a chiral oxazolidin-2-one or oxazolidin-2-thione having formula 2, produced from the reaction of N-protected 2-(2-methoxyphenoxy)ethylamine with a chiral glycidol derivative is used as a key intermediate for the preparation of the chiral carvedilol. Specifically, the process for the preparation of the chiral carvedilol comprises a) reacting a compound of formula 2 with a halogenation agent, a sulfonation agent or a mitsunobu reagent to activate a hydroxyl group of the compound of formula 2, followed by nucleophilic substitution reaction with 9H-4-hydroxy carbazole to produce a compound of formula 7, and b) subjecting the obtained compound of formula 7 to a deprotection reaction in a presence of an inorganic base to produce the targeted chiral carvedilol. The process of the present invention can be accomplished in a mild condition. The process neither requires any extraordinary purification procedure, nor involves decrease of optical purity. Therefore, the process of the present invention provides highly optical pure chiral carvedilol in simple and efficient manner.
  [FR] L'invention porte sur un procédé efficace de préparation de carvédilol chiral de haute pureté optique selon lequel on utilise comme intermédiaire clef une oxazolidin-2-one chirale ou une oxazolidin-2-thione chirale de formule (2) résultant de la réaction de 2-(2-méthoxyphénoxy)éthylamine protégée en N avec un dérivé chiral de glycidol. Le procédé de préparation consiste spécifiquement: a) faire réagir un composé de formule (2) avec un agent halogénant, un agent de sulfonation ou un réactif de Mitsunobu pour activer un groupe hydroxyle du composé de formule (2), puis à effectuer une réaction de substitution nucléophile avec du 9H-4-hydroxy carbazole pour obtenir le composé de formule (7); et b) à soumettre le composé de formule (7) à une réaction de déprotection en présence d'une base minérale pour obtenir le carvédilol chiral cible. Ledit procédé: peut s'exécuter dans des conditions modérées; ne nécessite pas de purification extraordinaire, sans que cela ne nuise à la pureté optique; et permet d'obtenir du carvédilol chiral de haute pureté optique, d'une manière simple et efficace.
• WO2007/97504
  申请人：——

  公开号：——

  公开（公告）日：——