(-)-(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid | 42399-47-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (-)-(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid
• 英文别名: (2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid；(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenyl)sulfanylpropanoic acid
• CAS: 42399-47-3
• 化学式: C₁₆H₁₅NO₆S
• 分子量: 349.364
• InChiKey: MAZQSTHKJABVOC-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 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：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid 生成 (2R,3R)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 、 methyl (2S,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenyl)sulfanylpropanoate 、 sodium hydroxide 生成 (-)-(2R,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid
  参考文献：
  名称：

  HASHIYAMA, TOMIKI;INOUE, HIROZUMI;KONDA, MIKIHIKO;TAKEDA, MIKIO, J. CHEM. SOC. PERKIN TRANS., 1984, N 8, 1725-1732

  摘要：

  DOI：

文献信息

• The practical resolution of (2RS,3RS)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid, a key intermediate for diltiazem, with L-lysine.
  作者：Masaru SENUMA、Masataka SHIBAZAKI、Shigeru NISHIMOTO、Keijiroh SHIBATA、Kimio OKAMURA、Tadamasa DATE

  DOI：10.1248/cpb.37.3204

  日期：——

  Practical resolution of (2RS, 3RS)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic acid (2) was examined by the use of several basic amino acids. L-Lysine was found to be the most effective resolving agent to obtain (+)-(2S, 3S)-2, a key intermediate for the synthesis of diltiazem (1). This new method should be applicable to the industrial production of 1 in view of the simplicity of the procedure, the ready availability of L-lysine, and the high yield of the desired isomer. The absolute stereochemistry of (+)-2 was determined to be 2S, 3S by X-ray crystallographic analysis.

  通过使用几种基本氨基酸，对(2RS, 3RS)-2-羟基-3-(4-甲氧基苯基)-3-(2-硝基苯硫)丙酸(2)的实际分离进行了研究。结果发现，L-赖氨酸是获得(+)-(2S, 3S)-2的最有效的分离剂，(+)-(2S, 3S)-2是合成地尔硫卓(1)的关键中间体。考虑到该方法的简便性、L-赖氨酸的易得性以及所需异构体的高产率，这种新方法应适用于1的工业生产。通过X射线晶体学分析，确定(+)-2的绝对立体化学构型为2S, 3S。
• PROCESS FOR PREPARING BEPOTASTINE AND INTERMEDIATES USED THEREIN
  申请人：Ha Tae Hee

  公开号：US20100168433A1

  公开（公告）日：2010-07-01

  A process for stereospecific preparation of bepotastine of formula (I) and novel intermediates used therein having formulae (II) to (IV) are provided. The inventive process comprises subjecting (RS)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine to a reaction with a 4-halobutanoic acid l-menthyl ester, halo being chloro, bromo or iodo, in an organic solvent in the presence of a base to produce (RS)-bepotastine l-menthyl ester of formula (II), conducting a reaction of the compound of formula (II) with N-benzyloxycarbonyl L-aspartic acid in an organic solvent to induce selective precipitation of bepotastine l-menthyl ester.N-benzyloxycarbonyl L-aspartate of formula (III), filtering the precipitates formed in step 2) to isolate the compound of formula (III), treating the compound of formula (III) with a base to liberate bepotastine l-menthyl ester of formula (IV), and hydrolyzing the compound of formula (IV) in the presence of a base. The inventive process can provide bepotastine having a high optical purity of not less than 99.5% in a high yield, and thus, is useful in the development of anti-histamines and anti-allergic agents.

  提供了一种用于立体特异性制备化学式(I)的倍他司汀以及在其中使用的具有化学式(II)至(IV)的新型中间体的方法。这种创新的方法包括将(RS)-4-[(4-氯苯基)(2-吡啶基)甲氧基]哌啶与一种有机溶剂中的碱反应，生成(RS)-倍他司汀l-薄荷酸薄荷酯化合物(II)，然后将化合物(II)与N-苄氧羰基L-天冬氨酸酸在有机溶剂中反应，诱导倍他司汀l-薄荷酸薄荷酯的选择性沉淀。将沉淀物在步骤2)中形成的化合物(III)进行过滤以分离出化合物(III)，然后用碱处理化合物(III)以释放倍他司汀l-薄荷酸薄荷酯化合物(IV)，最后在碱的存在下水解化合物(IV)。这种创新的方法可以提供具有99.5%以上高光学纯度且高收率的倍他司汀，因此在抗组胺药物和抗过敏药物的开发中非常有用。
• Acid addition salt of optically active piperidine compound and process for preparing the same
  申请人：UBE INDUSTRIES, LTD.

  公开号：US20020026054A1

  公开（公告）日：2002-02-28

  The present invention is to provide a benzenesulfonic acid salt and a benzoic acid salt of (S)-4-[4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidino]butanoic acid represented by the formula (I): 1 wherein * represents an asymmetric carbon, which are excellent in antihistaminic activity and anti-allergic activity, and a process for producing the same.

  本发明提供了一种苯磺酸盐和苯甲酸盐，其化学式为（I）：其中*代表不对称碳，该化合物具有出色的抗组胺活性和抗过敏活性，同时还提供了其制备方法。
• Acid-addition salts of optically active piperidine compound and process for producing the same
  申请人：Ube Industries, Ltd.

  公开号：US06307052B1

  公开（公告）日：2001-10-23

  The present invention is to provide a benzenesulfonic acid salt and a benzoic acid salt of (S)-4-[4-[(4-chlorophenyl) (2-pyridyl)methoxy]piperidino]butanoic acid represented by the formula (I): wherein * represents an asymmetric carbon, which are excellent in antihistaminic activity and anti-allergic activity, and a process for producing the same.

  本发明提供了一种苯磺酸盐和苯甲酸盐，它们是由式(I)所表示的(S)-4-[4-(4-氯苯基)(2-吡啶基)甲氧基]哌啶基丁酸的盐，其中*代表不对称碳，具有优异的抗组胺活性和抗过敏活性，以及其制备方法。
• ACID-ADDITION SALTS OF OPTICALLY ACTIVE PIPERIDINE COMPOUND AND PROCESS FOR PRODUCING THE SAME
  申请人：Ube Industries, Ltd.

  公开号：EP0949260B1

  公开（公告）日：2002-05-22