1-[(7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-[(7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium
• 英文别名: 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C19H25N6O5S2+
• 分子量: 481.6
• InChiKey: HVFLCNVBZFFHBT-FMCGGJTJSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  10

文献信息

• Process for preparing pure cephalosporine intermediates
  申请人：Parthasaradhi Reddy Bandi

  公开号：US20070111980A1

  公开（公告）日：2007-05-17

  The present invention relates to a process for preparing key intermediates for cephalosporin antibiotics substantially free of undesired Δ 2 isomer. Thus, 7-aminocephalosporanic acid (7-ACA) is silylated with hexamethyldisilazane in cyclohexane at reflux temperature. (6R,7R)-3-[(Acetyloxy)methyl]-7-(trimethylsilyl)aminoceph-3-em-4-oic acid obtained is reacted with the mixture of N-methylpyrrolidine and trimethylsilyl iodide in cyclohexane, desilylated with isopropyl alcohol and treated with hydrochloric acid to obtain [6R-(6α,7β)]-1-[[7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium inner salt hydrochloride. [6R-(6α,7β)]-1-[[7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium inner salt hydrochloride is N-acylated with syn-2-(2-aminothiazol-4-yl)-2-methoxyimino acetic acid 2-benzothiazolyl thioester (MAEM) followed by treatment with hydrochloric acid to give cefepime dihydrochloride monohydrate.

  本发明涉及一种制备头孢菌素抗生素关键中间体的方法，该方法基本上不含不需要的Δ2异构体。因此，将7-氨基头孢烷酸（7-ACA）在环己烷中回流温度下与六甲基二硅氮烷硅化，得到（6R，7R）-3-[(乙酰氧)甲基]-7-(三甲基硅基)氨基头孢-3-烯-4-酸，然后将其与N-甲基吡咯烷和三甲基硅基碘混合物在环己烷中反应，用异丙醇去除硅基，再用盐酸处理，得到[6R-(6α,7β)]-1-[[7-氨基-2-羧基-8-氧代-5-硫-1-氮杂双环[4.2.0]辛-2-烯-3-基]甲基]-1-甲基吡咯烷内盐盐酸盐。然后，用syn-2-(2-氨基噻唑-4-基)-2-甲氧基亚硝基乙酸2-苯并噻唑基硫酯（MAEM）对[6R-(6α,7β)]-1-[[7-氨基-2-羧基-8-氧代-5-硫-1-氮杂双环[4.2.0]辛-2-烯-3-基]甲基]-1-甲基吡咯烷内盐盐酸盐进行N-酰化，然后用盐酸处理，得到头孢哌酮二盐酸盐一水合物。
• Process for production of intermediates for use in cefalosporin synthesis
  申请人：Ludescher Johannes

  公开号：US20070191601A1

  公开（公告）日：2007-08-16

  The invention relates to a new process for the production of intermediates for the synthesis of caephalosporin of formula (I) wherein R 1 , R 2 and R 3 , independently of one another, are alkyl, alkenyl, aryl, hydroxy(C 1-6 )alkyl, carbamoyl-(C 1-6 )alkyl, amino-(C 1-6 )alkyl, acylamino-(C 1-6 )alkyl or carboxy(C 1-6 )alkyl, or wherein R 2 and R 3 together with the adjacent nitrogen atom, form an alicyclic 5- to 8-membered heterocyclic ring, and R 1 signifies alkyl, alkenyl or aryl. The process according to the invention is notable in that the formation of undesired by-products, especially Δ2-analogous compounds of formula (I), is greatly reduced.
• US7592447B2
  申请人：——

  公开号：US7592447B2

  公开（公告）日：2009-09-22