2-hydroxy 3-(4-methoxyphenyl)-3-(2-amino phenylthio)-propionic acid | 30193-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-hydroxy 3-(4-methoxyphenyl)-3-(2-amino phenylthio)-propionic acid
• 英文别名: 2-hydroxy-3-(2'-aminophenylthio)-3-(4''-methoxyphenyl)propionic acid；2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propanoic acid；3-(2-amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid；(+)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid；(2S,3S)-3-(2-aminophenyl)thio-2-hydroxy-3-(4-methoxybenzene)-propanoic acid；dl-α-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid；3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS: 30193-57-8
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: KHQWPNQLSKDWAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-hydroxy 3-(4-methoxyphenyl)-3-(2-amino phenylthio)-propionic acid 在 对甲苯磺酸一水合物 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以95.5%的产率得到cis-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one
  参考文献：
  名称：

  Process for preparing 1,5-benzothiazepine derivatives

  摘要：

  本文描述了一种制备1,5-苯并噻吩啉衍生物的过程。该过程涉及使用磺酸作为催化剂，以形成1,5-苯并噻吩啉环的环闭合。所得化合物具有众所周知的药物性质。

  公开号：

  US05128469A1
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-环氧乙烷羧酸乙酯 在 sodium hydroxide 作用下， 生成 2-hydroxy 3-(4-methoxyphenyl)-3-(2-amino phenylthio)-propionic acid
  参考文献：
  名称：

  Kugita,H. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 2028 - 2037

  摘要：

  DOI：

文献信息

• Process for preparing 1,5-benzothiazepin derivatives
  申请人：DSM N.V.

  公开号：EP0450705A1

  公开（公告）日：1991-10-09

  The invention relates to a process for preparing a preferably stereoisomerically pure 1,5-benzothiazepin derivative with the general formula (I) by the cyclization of an ester of the corresponding 2-hydroxy-3-(4-R₃-phenyl)--3-(2-aminoarylthio)propanoic acid with the general formula (II) in the presence of a base and in an aprotic, polar solvent where R₁ and R₂, each independently, represent hydrogen, halogen, or an alkyl group with 1-6 carbon atoms or together with the phenyl group to which they are attached from a naphtalene group, R₄ represents a residual group with 1-20 carbon atoms and R₃ a hydrogen atom, a hydroxy group or an alkoxy group with 1-6 carbon atoms, at which a 2-hydroxy-3-(4-R₃-phenyl)-3-(2-aminoarylthio)propanoic acid ester with the general formula (II) is cyclized in the presence of an alkali metal alkanolate as base. The invention also relates to a process for the preparation of alkylated and/or acylated 1,5-benzothiazepin derivatives and to the new compounds of (2X,3Y)-2-phenyl-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2X,3Y)-2-phenyl-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-di hydro-1,5-benzothiazepin-4(5H)-one and (2X,3Y)-2-phenyl--3-acetyloxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benz othiazepin-4(5H)-one, where X and Y each independently represent the R or S configuration. Application of 1,5-benzothiazepin derivatives, obtained according to the process of the present invention, in the preparation of pharmaceuticals and particularly in the preparation of diltiazem.

  该发明涉及一种制备偏好立体异构纯的1,5-苯并噻吩基衍生物的过程，其具有通式（I），通过在无水极性溶剂中，在碱的存在下，将相应的2-羟基-3-(4-R₃-苯基)-3-(2-氨基芳硫基)丙酸酯与通式（II）进行环化，其中R₁和R₂，各自独立地代表氢、卤素或具有1-6个碳原子的烷基基团，或与它们连接的苯基一起形成萘基，R₄代表具有1-20个碳原子的残基，R₃代表氢原子、羟基或具有1-6个碳原子的烷氧基，在碱金属烷醇盐存在下，通过环化2-羟基-3-(4-R₃-苯基)-3-(2-氨基芳硫基)丙酸酯与通式（II）。 该发明还涉及一种制备烷基化和/或酰化1,5-苯并噻吩基衍生物的过程以及新化合物(2X,3Y)-2-苯基-3-羟基-2,3-二氢-1,5-苯并噻吩-4(5H)-酮，(2X,3Y)-2-苯基-3-羟基-5-[2-(二甲氨基)乙基]-2,3-二氢-1,5-苯并噻吩-4(5H)-酮和(2X,3Y)-2-苯基-3-乙酰氧基-5-[2-(二甲氨基)乙基]-2,3-二氢-1,5-苯并噻吩-4(5H)-酮，其中X和Y各自独立地代表R或S构型。 根据本发明的过程获得的1,5-苯并噻吩基衍生物的应用，特别是在制备药物，尤其是地尔硫卓的制备中。
• Novel optically active carboxylic acid derivative l-lysine salt and process for production thereof
  申请人：Nihon Iyakuhin Kogyo Co., Ltd.

  公开号：EP0320532A1

  公开（公告）日：1989-06-21

  A novel salt of d-threo-2-hydroxy-3-(2-amino-phenylthio)-3-(4-methoxyphenyl)-propionic acid represented by the following formula (1) wherein C* represents the carbon atoms of the optically resolved molecules, with L-lysine. The above compound can be produced by reacting d1-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid with L-lysine or a metal salt of said propionic acid with an acid salt of L-lysine to form corresponding salts, and separating the difficultly-soluble salt from the resulting two optically active salts by utilizing the difference in solubility in a solvent between the two optically active salts. This compound is useful as a synthesis intermediate for a known pharmaceutical compound, diltiazem hydrochloride.

  下式(1)代表的 d-硫代-2-羟基-3-(2-氨基苯硫基)-3-(4-甲氧基苯基)-丙酸的新型盐 其中 C* 代表光解分子的碳原子、 与 L-赖氨酸。将 d1-苏氨酰-2-羟基-3-(2-氨基苯硫基)-3-(4-甲氧基苯基)-丙酸与 L-赖氨酸或上述丙酸的金属盐与 L-赖氨酸的酸盐反应生成相应的盐，并利用两种光学活性盐在溶剂中溶解度的差异，将难溶盐从生成的两种光学活性盐中分离出来，即可制得上述化合物。该化合物可用作已知药物化合物盐酸地尔硫卓的合成中间体。
• 2-Hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid, 8'-phenylmenthyl ester, especially for diltiazem
  申请人：MARION LABORATORIES, INC. (a Delaware corporation)

  公开号：EP0342904A3

  公开（公告）日：1991-01-30

  A method comprising steps of, first, contacting 4-methoxybenzaldehyde with a chloroacetic acid, (*)-8-phenylmenthyl ester, second, contacting the product from the first step with 2-aminothiophenol, by steps under conditions such that a (2*,3*)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid, (*)-8'-phenylmentthyl ester is prepared, third, hydrolyzing said propionic acid ester with an alkaline hydrolyzing agent, and fourth, contacting the product from the third step with an acid, by steps under conditions such that a (2*,3*)-2-hydroxy-3(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid is prepared. Optically active forms of the title compound are also claimed.

  一种方法，包括以下步骤：第一，将 4-甲氧基苯甲醛与氯乙酸、(*)-8-苯基孟硫基酯接触；第二，将第一步的产物与 2-氨基苯硫酚接触，通过步骤，在(2*,3*)-2-羟基-3-(4-甲氧基苯基)-3-(2-氨基苯硫基)丙酸的条件下，制备出(*)-8'-苯基孟硫基酯；第三，用碱性水解剂水解所述丙酸酯；第四，将第三步的产物与氯乙酸、(*)-8'-苯基孟硫基酯接触、(*)-8'-苯基孟硫基酯，第三步，用碱性水解剂水解所述丙酸酯，第四步，将第三步的产物与酸接触，这些步骤的条件是制备出(2*,3*)-2-羟基-3-(4-甲氧基苯基)-3-(2-氨基苯硫基)丙酸。该标题化合物的光学活性形式也已申请专利。
• Phenylglycidate stereoisomers, conversion products thereof with e.g. 2-nitrothiophenol and preparation of diltiazem
  申请人：DSM N.V.

  公开号：EP0343714A1

  公开（公告）日：1989-11-29

  The stereoisomerically pure esters of (2R,3S)-3-(4-hydroxy or 4-alkoxyphenyl)glycidic acid, which is a starting compound for the preparation of diltiazem, are prepared by stereospecific enzymatic hydrolysis. By using such an ester, it is possible to economically prepare the (2S,3S) isomer of diltiazem to the exclusion of other stereoisomers.

  (2R,3S)-3-(4-羟基或 4-烷氧基苯基)缩水甘油酯是制备地尔硫卓的起始化合物，其立体异构体纯酯是通过立体特异性酶水解制备的。通过使用这种酯类，可以经济地制备地尔硫卓的(2S,3S)异构体，而排除其他立体异构体。
• Process for the preparation of intermediates for the synthesis of diltiazem
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0353538A2

  公开（公告）日：1990-02-07

  A process for the preparation of (2S,3S)-threo-2-hydroxy-3-(2-­aminophenylthio)-3-(4-methoxyphenyl)-propionic acid by resolution of the racemic mixture is described. The resolution is carried out by using as resolving agent (1S,2S)­-threo-1-phenyl-2-amino-1,3-propanediol or (1S,2S)-threo-1-(4-­methylthiophenyl)-2-amino-1,3-propanediol.

  本发明描述了一种通过外消旋混合物的解析制备(2S,3S)-苏-2-羟基-3-(2-氨基苯硫基)-3-(4-甲氧基苯基)-丙酸的工艺。 解析是以(1S,2S)-1-苯基-2-氨基-1,3-丙二醇或(1S,2S)-1-(4-甲硫基苯基)-2-氨基-1,3-丙二醇作为解析剂进行的。