(+/-)-Carnitinnitril | 13613-60-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-Carnitinnitril
• 英文别名: (2-Hydroxy-3-cyan-propyl)-trimethyl-ammonium；4-Trimethylammonio-3-hydroxy-butyronitril；(3-cyano-2-hydroxy-propyl)-trimethyl-ammonium；(3-Cyan-2-hydroxy-propyl)-trimethyl-ammonium；(3-cyano-2-hydroxy-propyl)-trimethyl-ammonium cation；Ammonium, (3-cyano-2-hydroxypropyl)trimethyl-, chloride；(3-cyano-2-hydroxypropyl)-trimethylazanium
• CAS: 13613-60-0
• 化学式: C₇H₁₅N₂O
• 分子量: 143.209
• InChiKey: NZDSGBWRZXBCRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

文献信息

• PREPARATION METHOD OF HIGH-PURITY L-CARNITINE
  申请人：Gu Shuhua

  公开号：US20110263897A1

  公开（公告）日：2011-10-27

  The present invention relate to a preparation method of high-purity L-carnitine which belongs to an important technique of quality control in different steps of chiral medicine production. The method comprises the following steps of: monitoring the content of the L-isomer impurity in chiral material S-epichlorohydrin by gas chromatography and chiral column and controlling the content of the L-isomer impurity in chiral raw material in the definite range; monitoring and controlling the specific optical rotation of the chiral intermediate L-3-chloro-2-hydroxy-N,N,N-trimethyl-propanaminium in the definite ranges using a polarimeter; monitoring the content of the R-isomer in the intermediate L-3-cyano-2-hydroxy-N,N,N-trimethyl-propanaminium using derivation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC and controlling the content of the isomer in the intermediate in the definite range; and measuring the final product L-carnitine using derviation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC. This method gives the high-purity L-carnitine in which the content of L-isomer may be more than 97% and that of R-isomerless than 2%.

  本发明涉及高纯度L-肉碱的制备方法，属于手性药物生产不同步骤的质量控制的重要技术。该方法包括以下步骤：通过气相色谱和手性柱监测手性原料S-环氧氯丙烷中L-异构体杂质的含量，并控制手性原料中L-异构体杂质的含量在一定范围内；使用旋光仪监测和控制手性中间体L-3-氯-2-羟基-N，N，N-三甲基丙胺在一定范围内的比旋光度；通过HPLC使用衍生剂（+）α-甲基-6-甲氧基-2-萘乙酰氯监测中间体L-3-氰-2-羟基-N，N，N-三甲基丙胺中R-异构体的含量，并控制中间体中异构体的含量在一定范围内；通过HPLC使用衍生剂（+）α-甲基-6-甲氧基-2-萘乙酰氯测量最终产品L-肉碱。该方法可得到高纯度的L-肉碱，其中L-异构体的含量可达97%以上，R-异构体的含量小于2%。
• PROCESS FOR PRODUCTION OF BETAINE
  申请人：Oishi Kosuke

  公开号：US20090325246A1

  公开（公告）日：2009-12-31

  According to the present invention, by using 4-halogeno-3-hydroxybutanamide as a substrate in quaternary amination reaction with trialkylamine which is an important step in betaine (such as carnitine) preparation processes, it becomes possible to reduce the production of crotonic acid derivatives (the major by-product) greatly compared to conventional processes. Consequently, it becomes possible to prepare a betaine, such as carnitine, at a high yield. The present invention also relates to a process for preparing a betaine represented by formula (1) below, comprising a step of quaternary aminating an amide represented by formula (2) below: wherein A 1 , A 2 and A 3 individually represent a C 1 -C 20 hydrocarbon group which may have a substituent(s); and X 1 is a halogen atom.

  根据本发明，在甜菜碱（如肉碱）制备过程中，使用4-卤代-3-羟基丁酰胺作为底物与三烷基胺进行季铵化反应，可以大大减少与传统工艺相比产生的巴豆酸衍生物（主要副产物）。因此，可以高产得到甜菜碱（如肉碱）。本发明还涉及一种制备下式（1）所表示的甜菜碱的方法，包括季铵化下式（2）所表示的酰胺的步骤：其中A1、A2和A3分别表示可以具有取代基的C1-C20烃基；X1为卤素原子。
• Enantiomeric resolution of a carnitinamide salt by preferential crystallization
  申请人：UNIVERSITA' DEGLI STUDI DI MILANO

  公开号：EP1852416A1

  公开（公告）日：2007-11-07

  A process for the resolution of (D,L)-carnitinamide (D,L-I) chloride in its enantiomers (D-I) and (L-I), characterized in that a supersaturated solution or suspension of (D,L-I) in a suitable solvent or mixture of solvents, optionally added with a surfactant, is used. A series of alternate preferential crystallizations is carried out after adding minimum amount of seeds of one of the two enantiomers, (D-I) or (L-I), that is to be precipitated, and subsequently restoring the supersaturation conditions by adding an appropriate amount of (D,L-I) racemate.

  一种解决(D,L)-肉碱酰胺(D,L-I)氯化物的对映体(D-I)和(L-I)的过程，其特征在于使用适当溶剂或溶剂混合物中(D,L-I)超饱和溶液或悬浮液，可选地加入表面活性剂。在加入少量(D-I)或(L-I)中的一种对映体晶种后，进行一系列交替的优先结晶，并通过加入适量的(D,L-I)外消旋体恢复超饱和条件。
• Optisch aktive Salze aus einem substituierten Thiazolidin-4-carboxylat und 3-Cyano-2-hydroxypropyltrimethylammonium, deren Herstellung und Verwendung
  申请人：Degussa Aktiengesellschaft

  公开号：EP0456960A1

  公开（公告）日：1991-11-21

  Die Erfindung betrifft optisch aktive Salze der allgemeinen Formel (I) worin Ac eine Acylgruppe, R¹ Wasserstoff oder Methyl und R² und R³ gleiche oder unterschiedliche Substituenten, vorzugsweise Methyl bedeuten. Die Salze lassen sich aus der entsprechenden optisch aktiven Carbonsäure und DL-3-Cyano-2-hydroxypropyltrimethylammoniumhydroxid gewinnen. Die diastereomeren Salzpaare lassen sich leicht voneinander trennen und wieder spalten, so daß sich das Verfahren zur Herstellung von optisch aktiven 3-Cyano-2-hydroxypropyltrimethylammoniumsalzen eignet.

  本发明涉及通式 (I) 的光学活性盐 其中 Ac 是酰基，R¹ 是氢或甲基，R² 和 R³ 是相同或不同的取代基，最好是甲基。这些盐可以从相应的光学活性羧酸和 DL-3-Cyano-2-hydroxypropyltrimethylammonium hydroxide 中获得。非对映异构盐对很容易相互分离并再次裂解，因此该工艺适用于制备具有光学活性的 3-氰基-2-羟丙基三甲基铵盐。
• A PREPARATION METHOD OF HIGH-PURITY L-CARNITINE
  申请人：Changzhou Multiple Dimension Institute Of Industry Technology Co., Ltd.

  公开号：EP2360141B1

  公开（公告）日：2013-12-11