α-methyl-4-methoxyphenylalanine amide | 1343252-69-6

• 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: α-methyl-4-methoxyphenylalanine amide
• 英文别名: 2-(S)-Amino-3-(4-methoxyphenyl)-2-methylpropionamide；2-Amino-3-(4-methoxyphenyl)-2-methylpropanamide
• CAS: 1343252-69-6
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: XDYQSLSZAOGOBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-methyl-4-methoxyphenylalanine amide 在 potassium phosphate buffer 、 Mycobacterium neoaurum ATCC 25795 作用下， 反应 1.0h， 生成 甲基多巴EP杂质B
  参考文献：
  名称：

  微生物合成β-3-受体激动剂的手性中间体

  摘要：

  AbstractChiral intermediates were prepared by biocatalytic processes for the chemical synthesis of β‐3‐receptor agonists. These include: (i) the microbial reduction of 4‐benzyloxy‐3‐methanesulfonylamino‐2′‐bromoacetophenone 1 to the corresponding (R)‐alcohol 2 by Spingomonas paucimobilis SC 16113. In the biotransformation process, a reaction yield of >85% and an optical purity of 99.5% were obtained for the desired (R)‐alcohol 2; (ii) the enzymatic resolution of racemic α‐methyl phenylalanine amide, 3, and α‐methyl‐4‐hydroxy‐phenylalanine amide, 5, by amidase from Mycobacterium neoaurum ATCC 25795 to prepare the corresponding (S)‐amino acids 4 and 6. Reaction yields of 49.9 and 49 M% (theoretical maximum yield 50 M%) and optical purities of 99 and 94% were obtained for the desired (S)‐amino acids 4 and 6, respectively; (iii) the asymmetric hydrolysis of methyl‐(4‐methoxyphenyl)‐propanedioic acid, ethyl diester, 7, to the corresponding (S)‐monoester 8 by pig liver esterase. A reaction yield of 96 M% and an optical purity of 96% were obtained for (S)‐monoester 8 when reactions were carried out in a biphasic system containing 10% ethanol at 10°C.

  DOI：

  10.1007/s11746-998-0081-0

文献信息

• [EN] D-METYROSINE COMPOSITIONS AND METHODS FOR PREPARING SAME<br/>[FR] COMPOSITIONS DE D-MÉTYROSINE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：TYME INC

  公开号：WO2020197875A1

  公开（公告）日：2020-10-01

  The disclosure provides processes for preparing a compound of formula I, comprising reacting a compound of formula II with an aqueous acid in a solvent and at a temperature sufficient for at least about 48 hours to produce a compound of formula I: wherein, R1-R5 are defined herein. Also provided are D-metyrosine prepared according to the processes described herein and compositions comprising the D-metyrosine provided herein.

  该披露提供了制备式I化合物的过程，包括将式II化合物与溶剂中的水酸反应，在足够温度下反应至少约48小时，以产生式I化合物：其中，R1-R5在此处被定义。还提供了根据此处描述的过程制备的D-甲基酪氨酸，以及包含所提供的D-甲基酪氨酸的组合物。
• STEREOSELECTIVE SYNTHESIS OF METYROSINE
  申请人：HALLORAN Kevin John

  公开号：US20110104765A1

  公开（公告）日：2011-05-05

  Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.

  本文提供的是包含差向异构体在基本上差向异构体纯形式中的组合物以及包含基本上对映异构体纯形式的对映体，以及制备它们并将它们转化为甲基酪氨酸的过程。
• [EN] STEREOSELECTIVE SYNTHESIS OF METYROSINE<br/>[FR] SYNTHÈSE STÉRÉOSÉLECTIVE DE MÉTYROSINE
  申请人：ATON PHARMA INC

  公开号：WO2011053835A1

  公开（公告）日：2011-05-05

  Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.

  本文提供了包括对映异构体在基本上对映异构体纯形式和对映体在基本上对映体纯形式的组合物，以及制备它们和将它们转化为甲基酪氨酸的过程。
• Synthesis of optically pure .alpha.-alkylated .alpha.-amino acids and a single-step method for enantiomeric excess determination
  作者：Wim H. Kruizinga、John Bolster、Richard M. Kellogg、Johan Kamphuis、Wilhelmus H. J. Boesten、Emmo M. Meijer、Hans E. Schoemaker

  DOI：10.1021/jo00243a049

  日期：1988.4
• KRUIZINGA, WIM H.;BOLSTER, JOHN;KELLOGG, RICHARD M.;KAMPHUIS, JOHAN;BOEST+, J. ORG. CHEM., 53,(1988) N 8, 1826-1827
  作者：KRUIZINGA, WIM H.、BOLSTER, JOHN、KELLOGG, RICHARD M.、KAMPHUIS, JOHAN、BOEST+

  DOI：——

  日期：——