(S)-3-benzylamino-4-methyl-pentanoic acid | 608127-94-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-benzylamino-4-methyl-pentanoic acid
• 英文别名: (3S)-3-(benzylamino)-4-methylpentanoic acid
• CAS: 608127-94-2
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: CRGHGHLMEXVSAO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (rac)-3-benzylamino-4-methylpentanoic acid 生成 (S)-3-benzylamino-4-methyl-pentanoic acid 、 (R)-3-benzylamino-4-methyl-pentanoic acid
  参考文献：
  名称：

  通过以手性（salen）钴（III）配合物为对映选择性选择剂进行反复液-液萃取，可有效拆分外消旋的N-苄基β3-氨基酸。

  摘要：

  外消旋的N-苄基β（3）-氨基酸的有效（高达93％ee）分辨率已经通过使用亲脂性手性（salen）钴（III）配合物的迭代（两个周期）液-液萃取工艺实现了[ Co（III）（1）（OAc）]。通过萃取拆分的结果是，N-苄基β（3）-氨基酸的一种对映异构体在水相中占主导地位，而另一种对映异构体则通过络合成钴而被驱入有机相。然后，通过使用1-抗坏血酸的还原性（Co（III）→Co（II））反萃取将络合的氨基酸定量释放到水相中。还原裂解使钴（II）选择剂的回收率高达90％（可通过空气/ AcOH轻松再氧化为Co（III））。

  DOI：

  10.1039/b711477j

文献信息

• Process for producing either optically active n-substituted beta-amino acid and optically active n-substituted beta-amino acid ester or optically active n-substituted 2-homopipecolic acid and optically active n-substituted 2-homopipecolic acid ester
  申请人：Miyata Hiroyuki

  公开号：US20050170473A1

  公开（公告）日：2005-08-04

  The present invention discloses a process which comprises selectively hydrolyzing one enantiomer of racemic mixtures of an N-substituted β-amino acid alkyl ester or N-substituted 2-homopipecolic acid ester represented by the formula (I): wherein Ar, R 1 , R 2 , R 3 , R 4 and R 5 are the same as defined in the specification, in the presence of a hydrolase to form an optically active ((R) or (S))-N-substituted-β-amino acid or optically active ((R) or (S))-N-substituted 2-homopipecolic acid represented by the formula (II): and simultaneously to obtain an unreacted optically active ((S) or (R))-N-substituted β-amino acid alkyl ester or unreacted optically active ((S) or (R))-N-substituted 2-homopipecolic acid ester represented by the formula (III): which has a reverse steric absolute configuration to that of the compound represented by the formula (II).

  本发明揭示了一种过程，该过程包括在水解酶的存在下，选择性水解由公式（I）表示的N-取代β-氨基酸烷基酯或N-取代2-同环丙氨酸酯的混合物的一个对映体，其中Ar，R1，R2，R3，R4和R5与说明书中定义的相同，形成一个光学活性的（R）或（S）-N-取代β-氨基酸或光学活性的（R）或（S）-N-取代2-同环丙氨酸，其由公式（II）表示，并同时获得未反应的光学活性的（S）或（R）-N-取代β-氨基酸烷基酯或未反应的光学活性的（S）或（R）-N-取代2-同环丙氨酸酯，其由公式（III）表示，其具有与由公式（II）表示的化合物相反的立体绝对构型。
• PROCESS FOR PRODUCING EITHER OPTICALLY ACTIVE N-SUBSTITUTED BETA-AMINO ACID AND OPTICALLY ACTIVE N-SUBSTITUTED BETA-AMINO ACID ESTER OR OPTICALLY ACTIVE N-SUBSTITUTED 2-HOMOPIPECOLIC ACID AND OPTICALLY ACTIVE N-SUBSTITUTED 2-HOMOPIPECOLIC ACID ESTER
  申请人：Ube Industries, Ltd.

  公开号：EP1493819A1

  公开（公告）日：2005-01-05

  The present invention discloses a process which comprises selectively hydrolyzing one enantiomer of racemic mixtures of an N-substituted β-amino acid alkyl ester or N-substituted 2-homopipecolic acid ester represented by the formula (I):    wherein Ar, R1, R2, R3, R4 and R5 are the same as defined in the specification, in the presence of a hydrolase to form an optically active ((R) or (S))-N-substituted β-amino acid or optically active ((R) or (S))-N-substituted 2-homopipecolic acid represented by the formula (II): and simultaneously to obtain an unreacted optically active ((S) or (R))-N-substituted β-amino acid alkyl ester or unreacted optically active ((S) or (R))-N-substituted 2-homopipecolic acid ester represented by the formula (III): which has a reverse steric absolute configuration to that of the compound represented by the formula (II).

  本发明公开了一种工艺，该工艺包括选择性地水解由式（I）代表的 N-取代β-氨基酸烷基酯或 N-取代 2-高哌啶酸酯的外消旋混合物中的一种对映体： 其中 Ar、R1、R2、R3、R4 和 R5 与说明书中定义的相同、 在水解酶存在下，生成光学活性（(R)或(S)）-N-取代的 β-氨基酸或光学活性（(R)或(S)）-N-取代的由式（II）代表的 2-高代联哌醇酸： 并同时得到未反应的具有光学活性的((S)或(R))-N-取代的 β-氨基酸烷基酯或未反应的具有光学活性的((S)或(R))-N-取代的 2-高代联哌羧酸酯，由式(III)代表： 其立体绝对构型与式 (II) 所代表化合物的立体绝对构型相反。
• Nitrile Biotransformations for the Synthesis of Highly Enantioenriched β-Hydroxy and β-Amino Acid and Amide Derivatives: A General and Simple but Powerful and Efficient Benzyl Protection Strategy To Increase Enantioselectivity of the Amidase
  作者：Da-You Ma、De-Xian Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo800074k

  日期：2008.6.1

  Biotransformations of a number of racemic beta-hydroxy and beta-amino nitrile derivatives were studied using Rhodococcus erythropolis AJ270, the nitrile hydratase and amidase-containing microbial whole cell catalyst, under very mild conditions. The overall enantioselectivity of nitrile biotransformations was governed predominantly by the amidase whose enantioselectivity was switched on remarkably by an O- and a N-benzyl protection group of the Substrates. While biotransformations of beta-hydroxy and beta-amino alkanenitriles gave low yields of amide and acid products of very low enantiomeric purity, introduction of a simple benzyl protection group on the beta-hydroxy and beta-amino of nitrile substrates led to the formation of highly enantioenriched beta-benzyloxy and beta-benzylamino amides and acids in almost quantitative yield. The easy protection and deprotection operations, high chemical yield, and excellent enantioselectivity render the nitrile biotransformation a useful protocol in the synthesis of enantiopure beta-hydroxy and beta-amino acids.
• US7449325B2
  申请人：——

  公开号：US7449325B2

  公开（公告）日：2008-11-11
• Efficient resolution of racemic N-benzyl β3-amino acids by iterative liquid–liquid extraction with a chiral (salen)cobalt(iii) complex as enantioselective selector
  作者：Pawel Dzygiel、Chiara Monti、Umberto Piarulli、Cesare Gennari

  DOI：10.1039/b711477j

  日期：——

  The efficient (up to 93% ee) resolution of racemic N-benzyl beta(3)-amino acids has been achieved by an iterative (two cycle) liquid-liquid extraction process using a lipophilic chiral (salen)cobalt(III) complex [Co(III)(1)(OAc)]. As a result of the resolution by extraction, one enantiomer of the N-benzyl beta(3)-amino acid predominated in the aqueous phase, while the other enantiomer was driven into

  外消旋的N-苄基β（3）-氨基酸的有效（高达93％ee）分辨率已经通过使用亲脂性手性（salen）钴（III）配合物的迭代（两个周期）液-液萃取工艺实现了[ Co（III）（1）（OAc）]。通过萃取拆分的结果是，N-苄基β（3）-氨基酸的一种对映异构体在水相中占主导地位，而另一种对映异构体则通过络合成钴而被驱入有机相。然后，通过使用1-抗坏血酸的还原性（Co（III）→Co（II））反萃取将络合的氨基酸定量释放到水相中。还原裂解使钴（II）选择剂的回收率高达90％（可通过空气/ AcOH轻松再氧化为Co（III））。