p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide | 1273319-61-1

• 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: p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide
• 英文别名: (4-methoxyphenyl)methyl (6R,7R)-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;iodide
• CAS: 1273319-61-1
• 化学式: C₃₂H₃₂N₃O₅S*I
• 分子量: 697.594
• InChiKey: DBKKUPYXCNIMMZ-UVFMYQNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide 在 青霉素(酰胺)酶 、 硫酸 、 苯酚 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 11.0h， 生成 硫酸头孢匹罗
  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
• 作为产物：
  描述：

  2,3-环戊烯并吡啶 、 3-iodomethyl-7-phenylacetylamido-3-cephem-4-carboxylic acid p-methoxybenzyl ester 以 乙酸乙酯 为溶剂， 以5.04 g的产率得到p-methoxybenzyl 7-phenylacetamido-3-(2,3-cyclopenteno-1-pyridinio)-3-cephem-4-carboxylate iodide
  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

• One-Pot Synthesis of Cefpirome Sulfate from GCLE
  作者：Xuemin Duan、Yao Lu、Juan Han、Ligong Chen、Pengwu Zheng

  DOI：10.1080/00397911003629499

  日期：2011.2.7

  [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.