(R)-carnitinamide | 64532-04-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-carnitinamide
• 英文别名: [(2R)-4-amino-2-hydroxy-4-oxobutyl]-trimethylazanium
• CAS: 64532-04-3
• 化学式: C7H17N2O2+
• 分子量: 161.22
• InChiKey: KWIXGIMKELMNGH-ZCFIWIBFSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-carnitinamide 、 水 生成 左旋肉碱 、 铵
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Process for the preparation of R-(-)-carnitine
  申请人：——

  公开号：US20010031892A1

  公开（公告）日：2001-10-18

  R-(−)-carnitine is prepared by (a) conversion of (S)-3-hydroxy-4-butyrolactone [1] to alkyl (S)-4-halogen-3-hydroxy-butyrate [2] by reaction with a linear or branched C 1 -C 7 alcohol (b), substitution of a CN group for the halogen of compound [2] to yield the alkyl ester of (R)-4-cyano-3-hydroxybutyric acid [3], (c) conversion of alkyl ester [3] to yield (R)-4-cyano-3-hydroxybutyramide [4], (d) cyclization of compound [4] to yield (R)-5-(cyanomethyl)-2-oxazolidone [5] via conversion of the amide function to isocyanate, (e) hydrolysis of compound [5] to yield (R)-4-amino-3-hydroxybutyric acid [6], and finally (f) methylation of the amino group of compound [6] to yield the end product (R)-carnitine.

  (R)-(−)-肉碱的制备方法：(a)将(S)-3-羟基-4-丁酸内酯[1]与一种直链或支链的C1-C7醇[b]反应，得到烷基(S)-4-卤代-3-羟基丁酸酯[2]，(b)将化合物[2]的卤素替换为CN基，得到(R)-4-氰基-3-羟基丁酸酯[3]，(c)将烷基酯[3]转化为(R)-4-氰基-3-羟基丁酰胺[4]，(d)通过将酰胺功能团转化为异氰酸酯，使化合物[4]环化，得到(R)-5-(氰甲基)-2-噁唑烷酮[5]，(e)水解化合物[5]，得到(R)-4-氨基-3-羟基丁酸[6]，最后(f)将化合物[6]的氨基甲基化，得到最终产物(R)-肉碱。
• 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。
• Chemical process for the stereoselective synthesis of R-(-)- carnitine
  申请人：——

  公开号：US20010003135A1

  公开（公告）日：2001-06-07

  A process is described for the stereoselective synthesis of R-(−)-carnitine in which the characterizing step is condensation of glyerol with an amine of (−) camphorsulphonic acid.

  本文描述了一种立体选择性合成R-（-）肉碱的过程，其特征步骤是将甘油与（-）蒎磺酸胺缩合。
• Process for the preparation of (s)-beta-hydroxy-gamma-butyrolactone
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0765876B1

  公开（公告）日：1998-12-09