3-propenyl-7-amino-3-cephem-4-carboxylic acid

• 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-propenyl-7-amino-3-cephem-4-carboxylic acid
• 英文别名: 7-Amino-3-(prop-1-enyl)-3-cephem-4-carboxylic acid；7-amino-3-[(Z)-1-propen-1-yl]-3-cephem-4-carboxylic acid；7-Amino-3-[(Z)-1-propen-1-yl]ceph-3-em-4-carboxylic Acid；7-amino-3-[(Z)-1-propenyl]-3-cephem-4-carboxylic acid；7-Amino-3-[(Z)-prop-1-enyl]-3-cephem-4-carboxylic acid；(6R)-7-amino-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C₁₀H₁₂N₂O₃S
• 分子量: 240.283
• InChiKey: ZYLDQHILNOZKIF-AATZEOSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-propenyl-7-amino-3-cephem-4-carboxylic acid 、 benzotriazol-1-yl 2-[(Z)-2-aminothiazol-4-yl]-2-trityloxyiminoacetate 在 三甲基氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以131 g (100%, purity 96%)的产率得到7-[(Z)-2-(2-Aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-1-propenyl]-3-cephem-4-carboxylic Acid
  参考文献：
  名称：

  Process for cephem prodrug esters

  摘要：

  本发明揭示了一种选择性形成低级烷基2-(2-氨基噻唑-4-基)-2-氧代肟酸酯的氧代肟酰保护衍生物的过程，并将其用于7-氨基头孢菌素化合物的酰化。

  公开号：

  US04935508A1
• 作为产物：
  描述：

  benzhydryl 7-amino-3-[(Z)-1-propen-1-yl]-3-cephem-4-carboxylate 、 苯甲醚 在 乙醚 、 甲烷 、 盐酸 、 sodium hydroxide 、 水 、 丙酮 作用下， 以 三氟乙酸 为溶剂， 反应 6.17h， 生成 3-propenyl-7-amino-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Substituted vinylcephalosporins

  摘要：

  该公式表示的.beta.-内酰胺化合物为 ##STR1## 其中R.sup.5代表环丙基或甲基，可用作抗生素。

  公开号：

  US05171854A1

文献信息

• Method for preparation of ceftiofur and salts thereof
  申请人：LUPIN LIMITED

  公开号：US20040132996A1

  公开（公告）日：2004-07-08

  A process for preparation of ceftiofur sodium of formula (Ib) 1 possessing high stability and having purity of more than 97% and substantially free of impurities, is disclosed. The process comprises: i) reacting cefotaxime or its salts or its esters of formula (VI) 2 wherein R 3 is hydrogen, an alkali or alkaline earth metal, or an easily hydrolysable ester, with thiofuroic acid, employed in a molar proportion of 1.5 to 3.0 moles per mole of compound (VI), in the presence of acetonitrile as solvent and in the presence of large excess of methanesulfonic acid, employed in molar proportions of 12 to 18 moles per mole of compound (VI), and at a temperature of between −5° C. to 30° C. to give after necessary neutralisation of the alkali or alkaline earth metal or removal of the ester group of the 4-carboxylic acid function, wherever applicable, ceftiofur of formula (Ia), possessing high stability and having purity of more than 97% and substantially free of impurities; 3 ii) converting the ceftiofur of formula (Ia) thus obtained to its salt with an organic amine by treating a solution of ceftiofur in a mixture of water and a water-miscible organic solvent with an organic amine, at a temperature ranging from −10° C. to 10° C.; iii) reacting of the amine salt thus obtained with a sodium metal carrier in a mixture of water and water-miscible organic solvent and in presence of sodium hydrogen sulfite to give ceftiofur sodium of formula (Ib)

  揭示了一种制备具有高稳定性、纯度超过97%且基本无杂质的化学式为(Ib)1的头孢噻呋钠的方法。该方法包括：i) 在丙腈作为溶剂和大量过量的甲磺酸存在下，将头孢噻唑或其盐或其酯的化学式为(VI)2，其中R3为氢、碱金属或碱土金属，或易水解酯，与噻呋酸反应，摩尔比为每摩尔化合物(VI)1.5至3.0摩尔，温度在-5°C至30°C之间，经过必要的中和碱金属或碱土金属或去除4-羧基酸功能的酯基（如适用），得到具有高稳定性、纯度超过97%且基本无杂质的化学式为(Ia)的头孢噻呋；ii) 将得到的化学式为(Ia)的头孢噻呋转化为其与有机胺的盐，通过在水和水相溶性有机溶剂的混合物中用有机胺处理头孢噻呋的溶液，在温度范围为-10°C至10°C；iii) 在水和水相溶性有机溶剂的混合物中，以及在硫代亚硫酸氢钠存在下，将得到的胺盐与钠金属载体反应，得到化学式为(Ib)的头孢噻呋钠。
• 7-amino-3-propenylcephalosporanic acid and esters thereof
  申请人：Bristol-Meyers Company

  公开号：US04699979A1

  公开（公告）日：1987-10-13

  This invention provides novel cephalosporin intermediates, 7.beta.-amino-3-[(Z)-1-propen-1-y1]-3-cephem-4-carboxylic acid and esters thereof having the general formula ##STR1## wherein the configuration of the 3-propenyl group is Z sometimes referred to as cis- and R is hydrogen or a conventional carboxy-protected group, or a physiologically hydrolyzable esterifying group, and acid addition salts thereof and the metal salts of the foregoing substance wherein R is hydrogen. These compounds are useful as intermediates for preparation of orally active cephalosporins.

  这项发明提供了新颖的头孢菌素中间体，7-β-氨基-3-[(Z)-1-丙烯-1-基]-3-头孢-4-羧酸及其酯，其具有一般式##STR1##其中3-丙烯基基团的构型为Z，有时被称为顺式，R为氢或常规羧基保护基，或生理水解酯化基，以及其酸盐和前述物质的金属盐，其中R为氢。这些化合物可用作制备口服活性头孢菌素的中间体。
• Process for the preparation of 3-propenyl cephalosporin DMF solvate
  申请人：ORCHID CHEMICALS & PHARMACEUTICALS LIMITED

  公开号：US20040087786A1

  公开（公告）日：2004-05-06

  The present invention relates to an improved process for the preparation of 3-propenyl cephalosporin DMF solvate, more particularly, the present invention relates to an improved process for the preparation of cefprozil DMF solvate of the formula (I), which is useful for the preparation of cefprozil of the formula (XIV). 1

  本发明涉及一种改进的制备3-丙烯基头孢菌素DMF溶剂结晶体的方法，更具体地，本发明涉及一种改进的制备cefprozil DMF溶剂结晶体的方法，其化学式为(I)，该方法对于制备化学式为(XIV)的cefprozil非常有用。
• [EN] PROCESSES FOR THE PREPARATION OF CEPHALOSPORIN DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE CEPHALOSPORINE
  申请人：CJ CORP

  公开号：WO2005042544A1

  公开（公告）日：2005-05-12

  Provided is a process for preparing a compound of formula 1 or its salt. The process includes reacting a compound of formula 4 with acetaldehyde in a mixed solvent including water, isopropanol, and methylenechloride in a volume ratio of 1:3-6:11-14 in the presence of a first base to stereospecifically prepare a compound of formula 3 and reacting the compound of the formula 3 with an anhydrous compound of formula 2 in the presence of a second base.

  提供了一种制备化合物1或其盐的方法。该方法包括在水、异丙醇和二氯甲烷的混合溶剂中，以1:3-6:11-14的体积比例，将化合物4与乙醛在第一碱的存在下反应，立体特异性地制备化合物3，并将化合物3与无水化合物2在第二碱的存在下反应。
• [EN] PROCESSES FOR THE PREPARATION OF CEPHEM DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE CEPHEME
  申请人：CJ CORP

  公开号：WO2005042543A1

  公开（公告）日：2005-05-12

  Provided is a process for preparing a compound of formula 1 or its salt, which includes reacting a compound of formula 2 with a compound of formula 3 in the presence of a base.

  提供了一种制备化合物1或其盐的过程，包括在碱的存在下将化合物2与化合物3反应。