2-(RS)-[(2-amino-4-thiazolyl)methyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester | 192516-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(RS)-[(2-amino-4-thiazolyl)methyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
• 英文别名: racemic 2(R,S)-{(2-amino-4-thiazolyl)methyl}-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester；4-O-tert-butyl 1-O-methyl 2-[(2-amino-1,3-thiazol-4-yl)methyl]butanedioate
• CAS: 192516-60-2
• 化学式: C₁₃H₂₀N₂O₄S
• 分子量: 300.379
• InChiKey: XQCUHYXOHYTZQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(RS)-[(2-amino-4-thiazolyl)methyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester 在 sodium hydroxide 、 Alcalase 、 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 66.5h， 生成 2(R)-{(2-(1,1-dimethylethoxycarbonyl)amino-4-thiazolyl)methyl}-1,4-butanedioic Acid 4-(1,1-Dimethylethyl) Ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4
• 作为产物：
  描述：

  硫脲 、 2-((Z)-3-Bromo-2-hydroxy-allyl)-succinic acid 4-tert-butyl ester 1-methyl ester 以 乙腈 为溶剂， 反应 1.0h， 以55%的产率得到2-(RS)-[(2-amino-4-thiazolyl)methyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4

文献信息

• Stereoselective preparation of 2-substituted succinic acid derivatives
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US05808085A1

  公开（公告）日：1998-09-15

  A highly efficient and practical means has been developed which enables compounds of the formula: ##STR1## wherein R.sup.1 is lower alkoxy, lower alkylamino, di-(loweralkyl) amino, or the monovalent radical A--NR.sup.3, wherein A is lower alkyl or A is R.sup.4 R.sup.5 NC(O)CH.sub.2 wherein, for example, R.sup.4 is hydrogen or alkyl and R.sup.5 is hydrogen, alkyl or a substituted alkyl, or R.sup.5 is R.sup.6 R.sup.7 N-Alk wherein R.sup.6 and R.sup.7 each is hydrogen or lower alkyl and Alk is a divalent alkyl radical; R.sup.3 is, for example, benzyl, alkyl or a substituted alkyl; and R.sup.2 is, inter alia, alkyl, cycloalkyl, 1H-imidazol-4-yl, 4-thiazolyl or 2-amino-4-thiazolyl; to be prepared through the kinetic resolution of a compound of the formula: ##STR2## wherein R.sup.1 is as defined herein, R.sup.2 is as defined herein, and B is lower alkyl. These compounds are useful intermediates in the synthesis of renin inhibiting compounds.

  已经开发出一种高效实用的方法，可以制备式为：##STR1##其中R.sup.1是较低的烷氧基，较低的烷基氨基，二-(较低烷基)氨基，或单价基团A--NR.sup.3，其中A是较低的烷基或A是R.sup.4 R.sup.5 NC(O)CH.sub.2，其中，例如，R.sup.4是氢或烷基，R.sup.5是氢，烷基或取代烷基，或R.sup.5是R.sup.6 R.sup.7 N-Alk，其中R.sup.6和R.sup.7各自是氢或较低的烷基，Alk是双价烷基基团；R.sup.3是，例如，苄基，烷基或取代烷基；R.sup.2是，例如，烷基，环烷基，1H-咪唑-4-基，4-噻唑基或2-氨基-4-噻唑基等；通过动力学分辨制备式为：##STR2##其中R.sup.1，R.sup.2和B的定义如上所述。这些化合物是合成抑制肾素化合物的有用中间体。
• STEREOSELECTIVE PREPARATION OF 2-SUBSTITUTED SUCCINIC DERIVATIVES
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP0882138B1

  公开（公告）日：2000-07-05
• US5808085A
  申请人：——

  公开号：US5808085A

  公开（公告）日：1998-09-15