(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride | 77361-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride
• 英文别名: 4-bromo-2-methoxyimino-3-oxo-butyryl chloride；4-bromo-2(Z)-methoxyimino-3-oxobutyryl chloride；4-bromo-2-methoxyimino-3-oxobutyryl chloride；(2Z)-4-bromo-2-methoxyimino-3-oxobutanoyl chloride
• CAS: 77361-11-6
• 化学式: C₅H₅BrClNO₃
• 分子量: 242.457
• InChiKey: STQLBWSBVJOFBE-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride 生成 (6R,7R)-7-[[(2Z)-4-bromo-2-methoxyimino-3-oxobutanoyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  REINER, ROLAND;WEISS, URS

  摘要：

  DOI：
• 作为产物：
  描述：

  (2Z)-4-溴-2-(甲氧基亚胺)-3-氧代-丁酸 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride
  参考文献：
  名称：

  Method for manufacture of ceftriaxone sodium

  摘要：

  公开了一种改进的制备式（II）头孢曲松钠的方法。

  公开号：

  US20050059820A1

文献信息

• [EN] NOVEL INTERMEDIATES FOR SYNTHESIS OF CEPHALOSPORINS AND PROCESS FOR PREPARATION OF SUCH INTERMEDIATES<br/>[FR] NOUVEAUX INTERMEDIAIRES POUR LA SYNTHESE DE CEPHALOSPORINES ET LEUR PROCEDE DE PREPARATION
  申请人：LUPIN LTD

  公开号：WO2004058695A1

  公开（公告）日：2004-07-15

  A novel 4-halo-2-oxyimino-3-oxo butyric acid-N, N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics, wherein X is chlorine or bromine; R is hydrogen, C1-4 alkyl group, an easily removable hydroxyl protective group, -CH2COOR5, or -C(CH3)2COOR5, wherein R5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV1), wherein X, R and R5 are as defined above, with N, N-dimethylformiminium chloride chlorosulphate of formula (VII), in an organic solvent at a temperature ranging from -30 °C to -15 °C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.

  一种新型的4-卤代-2-氧基亚胺基-3-酮丁酸-N，N-二甲基甲酰氯氯磺酸盐化合物，化学式为(I)，用于头孢菌素抗生素的制备，其中X为氯或溴；R为氢、C1-4烷基、易于去除的羟基保护基、-CH2COOR5，或-C(CH3)2COOR5，其中R5为氢或易水解的酯基。化合物的化学式(I)通过将化学式(IV1)中的4-卤代-2-氧基亚胺基-3-酮丁酸（其中X、R和R5如上定义）与化学式(VII)中的N，N-二甲基甲酰氯氯磺酸盐在有机溶剂中在-30°C至-15°C的温度范围内反应制备。从中间体制备的头孢菌素包括头孢地尼尔、头孢地伦匹沃希、头孢吡肟、头孢他美匹沃希、头孢克烯、头孢美诺西、头孢地西美、头孢西利斯、头孢噻肟、头孢哌酮、头孢多酯普罗西替、头孢喹诺酮、头孢他唑啉、头孢替拉匹沃希、头孢替呋咐、头孢替唑酮、头孢三嗪和头孢唑纳。
• Ceftiofur, its intermediate and a process for the preparation of the same
  申请人：——

  公开号：US20020028931A1

  公开（公告）日：2002-03-07

  A novel process for the preparation of ceftiofur, a cephalosporin antibiotic useful in the treatment of bovine respiratory disease. The process utilizes a new bromo or chloro intermediate that can be isolated in a pure form by this inventive process subsequently resulting in ceftiofur of high purity. This invention offers a new-to-the-world route to Ceftiofur using novel intermediates.

  一种用于制备头孢菌素抗生素头孢噻呋的新工艺，该抗生素可用于治疗牛呼吸道疾病。该工艺利用一种新的溴或氯中间体，可以通过这一创新工艺纯化得到，从而得到高纯度的头孢噻呋。这一发明提供了一种新颖的头孢噻呋制备途径，利用了新颖的中间体。
• Method for production of t-butyl 3-oxobutyrates and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05109131A1

  公开（公告）日：1992-04-28

  Disclosed are an advantageous method of industrial production of tert-butyl 3-oxobutylate, which is a useful intermediate for synthesis, characterized by reacting tert-butyl alcohol with diketene in the presence of 4-(tertiary amino) pyridine, and an industrially advantageous method of producing cephalosporin compounds or pharmaceutically acceptable salts thereof, using tert-butyl 3-oxobutylate as an intermediate.

  本发明公开了一种工业生产3-氧代丁酸叔丁酯的优越方法，该方法以4-(三级胺)吡啶存在下，将叔丁醇与二酮反应，该化合物是合成的有用中间体。同时，本发明还公开了一种工业上有利的方法，使用3-氧代丁酸叔丁酯作为中间体，生产头孢菌素化合物或其药学上可接受的盐。
• Acyl derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04458072A1

  公开（公告）日：1984-07-03

  There are presented compounds of the formula ##STR1## wherein R.sup.1 is one of the 3-substituents usable in cephalosporin chemistry, R.sup.2 is hydrogen, lower alkyl or COOR.sup.3 -lower alkyl, wherein R.sup.3 is hydrogen, a cation of a base or a readily hydrolyzable ester group, and X is sulphur, oxygen or one of the groups --SO-- and --SO.sub.2 --, and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of these compounds and hydrates of the compounds of formula I or of their esters, ethers and salts, also presented are methods for the manufacture of these compounds as well as compounds used in their manufacture.

  公式##STR1##中呈现了化合物，其中R.sup.1是头孢菌素化学中可用的3-取代基之一，R.sup.2是氢、较低的烷基或COOR.sup.3-较低的烷基，其中R.sup.3是氢、一种碱的阳离子或易水解的酯基团，X是硫、氧或--SO--和--SO.sub.2--中的一种基团，以及这些化合物的易水解酯、易水解醚和盐，以及公式I的化合物或其酯、醚和盐的水合物，还提供了制造这些化合物的方法以及用于制造它们的化合物。
• 4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04845257A1

  公开（公告）日：1989-07-04

  A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

  生产4-卤代-2-(取代或未取代)羟基亚胺基-3-氧代丁酸酯或酰胺的方法，该方法是一种用于生产含有氨基噻唑基团头孢菌素的合成中间体，其特征在于将2-(取代或未取代)羟基亚胺基-3-氧代丁酸或其酯或酰胺与硅化剂反应，然后将所得的新型2-(取代)羟基亚胺基-3-硅氧基-3-丁烯酸酯或酰胺与卤代试剂反应。