3-[((R)-carboxy-phenyl-methyl)-amino]-but-2-enoic acid methyl ester; sodium salt | 13291-96-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 3-[((R)-carboxy-phenyl-methyl)-amino]-but-2-enoic acid methyl ester; sodium salt
• 英文别名: sodium (R)-N-(1-methoxycarbonylpropen-2-yl)-α-aminophenylacetate；Sodium N-[1-Methyl-2-carbomethoxyvinyl]-D(-)-alpha-aminophenylacetate；sodium;(2R)-2-[(4-methoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetate
• CAS: 13291-96-8
• 化学式: C₁₃H₁₄NO₄*Na
• 分子量: 271.248
• InChiKey: VWAWMPXOFHGGMY-UTONKHPSSA-M

物化性质

• 熔点：
  245-246 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.85
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 3-[((R)-carboxy-phenyl-methyl)-amino]-but-2-enoic acid methyl ester; sodium salt 以 丙酮 为溶剂， 反应 0.5h， 生成 (2Ξ,4R)-2-methoxycarbonylmethyl-2-methyl-5-oxo-4-phenyl-oxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  New Reactions and Reagents. III. The Reaction of Enamine Protected Amino Acids With Alkyl Chloroformates. Formation of 1,3-Oxazolidin-5-ones

  摘要：

  DOI：

  10.1055/s-1975-23907

文献信息

• Chemistry of cephalosporin antibiotics. 30. 3-Methoxy- and 3-halo-3-cephems
  作者：Robert R. Chauvette、Pamela A. Pennington

  DOI：10.1021/jm00238a017

  日期：1975.4

  the 3-hydroxy compounds to 3-methoxy-3-cephem derivatives. Removal of the ester-protecting group at the C4-carboxyl afforded a select group of cephalosporins with direct halo and methoxy substitution at C3. A number of these compounds are potent antibiotics.

  将7-酰基酰胺基和7-氨基-3-亚甲基头孢的酯中的外亚甲基臭氧化，得到3-羟基-3-头孢。描述了影响3-羟基-3-头皮核酸酯的选择性N-酰化的条件。Vilsmeier试剂将7-酰基-氨基-3-羟基化合物转化为3-卤-3-头孢酮衍生物。重氮甲烷将3-羟基化合物转化为3-甲氧基-3-头孢烯衍生物。除去C 4-羧基上的酯保护基团，得到选择的头孢菌素基团，其在C 3上具有直接的卤素和甲氧基取代。这些化合物中有许多是有效的抗生素。
• Process for preparing penicillin antibiotics
  申请人：Glaxo Laboratories Limited

  公开号：US03971775A1

  公开（公告）日：1976-07-27

  .alpha.-Aminoacylpenicillin antibiotics such as ampicillin and amoxycillin may be prepared in particularly simple manner by a process which comprises preparing a solution of 6-aminopenicillanic acid (6-APA) in a water-immiscible organic solvent by treating 6-APA with an excess of a strong tertiary amine base in the presence of said solvent; neutralising the residual strong tertiary amine base in said solution; reacting the neutralised solution with a solution in a water-immiscible organic solvent of an acylating agent which is a mixed anhydride of a lower alkoxyformic acid and an N-protected derivative of an .alpha.-aminoacid wherein the N-protecting group is acid-labile, to yield a solution of an N-protected .alpha.-aminoacylpenicillin derivative; contacting the resulting solution with water and a strong acid to cleave the acid-labile N-protecting group; and isolating the thus-obtained .alpha.-aminoacylpenicillin from the resulting water-containing system. The use of water-immiscible solvents in the process obviates the need for a solvent evaporation stage during isolation of the .alpha.-aminoacylpenicillin product and thus renders the process of particular advantage in plant-scale operations.

  .alpha.-氨基酰青霉素类抗生素，如氨苄青霉素和阿莫西林，可以通过以下简单的方法制备：首先将6-氨基青霉烷酸（6-APA）与过量的强三级胺碱在不溶于水的有机溶剂中反应，以制备6-APA的溶液；然后中和溶液中残留的强三级胺碱；接着将中和后的溶液与不溶于水的有机溶剂中的酰化试剂反应，该酰化试剂是较低的烷氧基甲酸和一种α-氨基酸的N-保护衍生物的混合酸酐，其中N-保护基为酸敏感，以产生一种N-保护的α-氨基酰青霉素衍生物的溶液；然后将所得溶液与水和强酸接触，以裂解酸敏感的N-保护基；最后从所得含水体系中分离出α-氨基酰青霉素。该过程中使用的不溶于水的溶剂消除了α-氨基酰青霉素产品的分离过程中需要蒸发溶剂的需求，因此在工厂规模的操作中具有特殊优势。
• Substituent effects upon the base hydrolysis of penicillins and cephalosporins. Competitive intramolecular nucleophilic amino attack in cephalosporins
  作者：Joseph M. Indelicato、Theresa T. Norvilas、Ralph R. Pfeiffer、William J. Wheeler、William L. Wilham

  DOI：10.1021/jm00251a011

  日期：1974.5
• New Reactions and Reagents. III. The Reaction of Enamine Protected Amino Acids With Alkyl Chloroformates. Formation of 1,3-Oxazolidin-5-ones
  作者：S. K. GUPTA

  DOI：10.1055/s-1975-23907

  日期：——