7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid | 128454-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
• 英文别名: 7-(Z)-[2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid；7-[2-(aminothiazol-4-yl)-2-(trityloxyimino)-acetamido]-3-vinyl-3-cephem-4-carboxylic acid；(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 128454-32-0
• 化学式: C₃₃H₂₇N₅O₅S₂
• 分子量: 637.74
• InChiKey: WGSAQWJPRKFPOA-DPWDVWKBSA-N

物化性质

• 熔点：
  165-166 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid 在 甲酸 作用下， 反应 3.0h， 以2.54 g的产率得到头孢地尼
  参考文献：
  名称：

  An alternative procedure for preparation of cefdinir

  摘要：

  Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7beta-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7beta-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3-vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.

  DOI：

  10.1016/s0014-827x(03)00063-6
• 作为产物：
  描述：

  羟甲基-7-氨基头孢烷酸 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 五氯化磷 、 sodium carbonate 、 苯甲醚 、 N,N-二甲基苯胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙酸乙酯 为溶剂， 反应 14.08h， 生成 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
  参考文献：
  名称：

  An alternative procedure for preparation of cefdinir

  摘要：

  Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7beta-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7beta-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3-vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.

  DOI：

  10.1016/s0014-827x(03)00063-6

文献信息

• [EN] PROCESS FOR THE PREPARATION OF CEFDINIR<br/>[FR] PROCEDE DE FABRICATION DE CEFDINIR
  申请人：RANBAXY LAB LTD

  公开号：WO2003091261A1

  公开（公告）日：2003-11-06

  The present invention relates to a process for the preparation of cefdinir on an industrial scale.

  本发明涉及一种用于工业规模制备头孢地尼尔的方法。
• [EN] CRYSTALLINE CEFDINIR SALTS<br/>[FR] SELS CEFDINIR CRISTALLINS
  申请人：ANTIBIOTICOS SPA

  公开号：WO2004056835A1

  公开（公告）日：2004-07-08

  Cefdinir crystalline salts of formula (I), in which n ranges from 1 to 3, the preparation and use thereof for the preparation and purification of cefdinir is herein disclosed. The salts of formula (I) can be obtained from cefdinir intermediates or crude cefdinir by treatment with phosphoric acid.

  本文披露了公式（I）中n的范围为1至3的头孢替尼结晶盐的制备和使用，用于头孢替尼的制备和纯化。公式（I）的盐可以通过用磷酸处理头孢替尼中间体或原始头孢替尼而获得。
• Process for the preparation of cefdinir
  申请人：Kumar Yatendra

  公开号：US20060040915A1

  公开（公告）日：2006-02-23

  The present invention relates to a process for the preparation of cefdinir on an industrial scale.

  本发明涉及一种工业规模制备头孢地尼尔的方法。
• CEFDINIR PROCESS
  申请人：PARTHASARADHI REDDY Bandk

  公开号：US20080287673A1

  公开（公告）日：2008-11-20

  The present invention provides an improved process for the preparation of high assayed cefdinir. Thus, crude cefdinir is added to water at 25-30° C. and then 18% hydrochloric acid is slowly added to form a clear solution. The solution is cooled to −5° C. and stirred for 5 minutes at −5° C. to +5° C. Then temperature of the mass is raised to 35-38° C., stirred for 15 minutes at the same temperature. To the reaction mass eno carbon is added at 35-38° C. and stirred for 30 minutes at 35-38° C. Then the contents are filtered on hiflo bed and washed with water. The filtrate is then cooled to 25° C., the pH is slowly adjusted to 2.6 with saturated sodium bicarbonate solution and stirred for 60 minutes at 25-30° C. Filtered the solid, washed with water and dried at 40° C. under vacuum to give high assayed cefdinir.

  本发明提供了一种改进的高纯头孢呋辛制备工艺。因此，将粗头孢呋辛加入25-30℃的水中，然后缓慢加入18％的盐酸以形成清澈的溶液。将溶液冷却至-5℃并在-5℃到+5℃之间搅拌5分钟。然后将物质的温度升至35-38℃，在相同的温度下搅拌15分钟。在35-38℃下向反应物中加入乙烯碳，搅拌30分钟。然后将内容物在hiflo床上过滤并用水洗涤。然后将滤液冷却至25℃，缓慢用饱和的碳酸氢钠溶液调节pH至2.6，并在25-30℃下搅拌60分钟。过滤固体，用水洗涤并在真空下40℃干燥，即可得到高纯头孢呋辛。
• Prasada Rao; Dandala, Ramesh; Sivakumaran, Meenakshisunderam, Journal of Heterocyclic Chemistry, 2007, vol. 44, # 2, p. 309 - 314
  作者：Prasada Rao、Dandala, Ramesh、Sivakumaran, Meenakshisunderam、Rani, Ananta、Naidu

  DOI：——

  日期：——