3-tert-Butoxycarbonylamino-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 203434-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-tert-Butoxycarbonylamino-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: 1,1-Dimethylethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-1-pyrrolidinecarboxylate；tert-butyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxopyrrolidine-1-carboxylate
• CAS: 203434-47-3
• 化学式: C₁₄H₂₄N₂O₅
• 分子量: 300.355
• InChiKey: OMZMWEJIEUFCRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄氧基胺盐酸盐 、 3-tert-Butoxycarbonylamino-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 吡啶 作用下， 反应 3.5h， 以63%的产率得到
  参考文献：
  名称：

  Synthesis, antimycobacterial and antibacterial activity of l-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives containing an oxime-functionalized pyrrolidine moiety

  摘要：

  A series of novel 1-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives 21-24 containing an oxime-functionalized pyrrolidine moiety were designed, synthesized and evaluated for their biological activity. Our results reveal that compounds 21a, 21e and 21j show considerable activity against MTB H37Rv ATCC 27294 (MICs: <0.25 mu g/mL) and MDR-MTB 6133 (MICs: 0.03-0.054 lg/mL). The target compounds 21-24 are generally poor against the Gram-negative strains, but 21a-j and 22a-c have potent potency (MICs: <0.008-32 mu g/mL) against all of the tested Gram-positive strains including MRSA and MRSE with a few exceptions, and the most active compounds 21d, 21e and 22a-c (MICs: <0.008-32 mu g/mL) were found to be comparable to or better than moxifloxacin, and 2->250 times more potent than ciprofloxacin and levofloxacin. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.027
• 作为产物：
  描述：

  N-Boc-3-吡咯啉 在 sodium azide 、 pyridine*SO₃*Et₃N 、 ammonium chloride 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 生成 3-tert-Butoxycarbonylamino-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Methyloxime-substituted aminopyrrolidine: A new surrogate for 7-basic group of quinolone

  摘要：

  Novel fluoroquinolones containing oxime functionalized aminopyrrolidines have been synthesized. They were found to possess potent antibacterial activities against both Gram-negative and Gram-positive organisms, including methicillin resistant Staphylococcus aureus (MRSA). Among these compounds, LB20277 (compound 12) showed the most favorable in vivo efficacy and pharmacokinetic profile in animals. Based on these promising results, LB20277 was selected as a candidate for further evaluation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10222-0