2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate
• 英文别名: (2-sulfanylidene-3H-1,3-benzothiazol-4-yl) (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate
• 化学式: C₁₃H₁₀N₄O₃S₃
• 分子量: 366.445
• InChiKey: AHNGYHDSEACHGA-MFOYZWKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate 、 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 头孢匹罗
  参考文献：
  名称：

  One-Pot Synthesis of Cefpirome Sulfate from GCLE

  摘要：

  [image omitted] Cefpirome was synthesized in 37.7% overall yield from 3-chloromethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GCLE) by sequential substitution of C-3 chloride with iodide and 2,3-cyclopentenopyridine, followed by a one-pot procedure including deprotection of carboxyl group, hydrolysis of 7-phenylacetamido, and reaction with 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (MAEM). The reaction conditions were as follows: obtained from GCLE at low temperature (-5 to 0 degrees C) and absence of light, 3-iodomethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GILE) without purification was reacted directly with 2,3-cyclopentenopyridine, in which the molar ratio of GCLE, NaI, and 2,3-cyclopentenopyridine was 1:2:4, and the molar ratio of the resulting compound p-methoxybenzyl 7-phenylacetylamido-3-(2,3-cyclopenteno-1-pyridinio)methyl-3-cephem-4-carboxylate iodide and MAEM was 1:1.1. The structure of the intermediate and the target compound obtained were determined by nuclear magnetic resonance spectra and mass spectroscopy.

  DOI：

  10.1080/00397911003629499

文献信息

• [EN] PROCESS FOR PREPARATION OF CEFEPIME DIHYDROCHLORIDE MONOHYDRATE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DICHLORHYDRATE DE CÉFÉPIME MONOHYDRATÉ
  申请人：NECTAR LIFESCIENCES LTD

  公开号：WO2011121389A1

  公开（公告）日：2011-10-06

  A process for preparation of cefepime dihydrochloride monohydrate is provided. The process comprises condensing 7-amino-3-[(l -methyl- 1 -pyrrolidino)methyl]-3-cephem-4-carboxylate monohydrochloride dihydrate and 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate in the presence of a base in an alcohol solvent.

  提供一种制备头孢匹罗啉二盐酸盐一水合物的方法。该方法包括在醇溶剂中，在碱的存在下，将7-氨基-3-[(l-甲基-1-吡咯啉基)甲基]-3-头孢-4-羧酸单盐酸盐二水合物和2-巯基苯并噻唑基-(Z)-2-(2-氨基噻唑-4-基)-2-甲氧基亚胺乙酸酯进行缩合。
• [EN] A NEW PROCESS FOR THE PREPARATION OF CEFDITOREN USING THE THIOESTER OF THIAZOLYLACETIC ACID<br/>[FR] NOUVELLE METHODE DE PREPARATION DE CEFDITORENE UTILISANT LE THIOESTER D'ACIDE THIAZOLYLACETIQUE
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2003099826A1

  公开（公告）日：2003-12-04

  The present invention provides a process for the preparation of Cefditoren of formula (I) which comprises acylating 7-amino-cephem carboxylic acids of the general formula (IV), where R3 is hydrogen or trimethylsilyl with thioester derivatives of the formula (II), where R1 represents C1 - C4 alkyl or phenyl in an organic solvent in the presence of an organic base at a temperature in the range of -10 °C to 30 °C.

  本发明提供了一种制备式（I）的头孢地妥酯的方法，该方法包括在有机溶剂中，在有机碱的存在下，将一般式（IV）的7-氨基-头孢菌素羧酸（其中R3为氢或三甲基硅基）与一般式（II）的硫酯衍生物（其中R1代表C1-C4烷基或苯基）酰化，反应温度在-10°C至30°C范围内。
• Process for the preparation of cefditoren using the thioester of thiazolylacetic acid
  申请人：——

  公开号：US20030225265A1

  公开（公告）日：2003-12-04

  The present invention provides a process for the preparation of Cefditoren of formula (I) 1 which comprises acylating 7-amino-cephem carboxylic acids of the general formula (IV), where R 3 is hydrogen or trimethylsilyl with thioester derivatives of the formula (II), where R 1 represents C 1 -C 4 alkyl or phenyl in an organic solvent in the presence of an organic base at a temperature in the range of −10 ° C. to 30 ° C.

  本发明提供了一种制备式Cefditoren（I）的过程，该过程包括在有机溶剂中，在有机碱的存在下，将一般式（IV）的7-氨基-头孢菌素羧酸（其中R3为氢或三甲基硅基）与一般式（II）的硫酯衍生物（其中R1代表C1-C4烷基或苯基）酰化，温度范围为-10°C至30°C。
• Process for the production of cefotaxime sodium
  申请人：Jaweed Mukarram Mohammed Siddiqui

  公开号：US20070004916A1

  公开（公告）日：2007-01-04

  A process for the production of 7-[2-(2-amino-4-thiazolyl)-2-syn-methoxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (Cefotaxime) in aqueous isopropyl alcohol is provided. The synthesis provides the product in greater than 99 % HPLC purity.

  提供了一种在水中异丙醇中生产7-[2-(2-氨基-4-噻唑基)-2-合成-甲氧基亚胺基乙酰胺基]-3-乙酰氧甲基-3-头孢基-4-羧酸（头孢噻肟）的过程。合成过程可以提供高于99%的HPLC纯度的产品。
• [EN] PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS<br/>[FR] PROCEDE DE PREPARATION D'ANTIBIOTIQUES CEPHALOSPORINES
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2004037833A1

  公开（公告）日：2004-05-06

  The present invention more particularly relates to a process for the preparation of cephalosporin antibiotics of the formula (I) wherein R1 represents hydrogen, trityl, CH3, CRaRbCOORYc where Ra and Rb independently represent hydrogen or methyl and Rc represents hydrogen or (C1-C6)alkyl; R2 is carboxylate ion or COORd, where Rd represents hydrogen, ester or a counter ion which forms a salt; R3 represents hydrogen, CH3, CH2OCOCH3, CH=CH2.

  本发明更具体地涉及一种制备头孢菌素抗生素的方法，其中该抗生素的化学式为(I)，其中R1代表氢、三苯甲基、CH3、CRaRbCOORYc，其中Ra和Rb独立地代表氢或甲基，Rc代表氢或(C1-C6)烷基；R2为羧酸根离子或COORd，其中Rd代表氢、酯或形成盐的对离子；R3代表氢、 、 OCO 、CH=CH2。