(Pyrrolidin-3-ylcarbamoylmethyl)-carbamic acid tert-butyl ester | 140412-70-0

• 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: (Pyrrolidin-3-ylcarbamoylmethyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-oxo-2-(pyrrolidin-3-ylamino)ethyl]carbamate
• CAS: 140412-70-0
• 化学式: C₁₁H₂₁N₃O₃
• 分子量: 243.306
• InChiKey: BZIBDVNQOJVQNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Pyrrolidin-3-ylcarbamoylmethyl)-carbamic acid tert-butyl ester 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 7.0h， 生成 7-[3-(2-Amino-acetylamino)-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; hydrochloride
  参考文献：
  名称：

  Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity

  摘要：

  A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3-quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparatively solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S-(R*,R*)]-7-[3-[2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).

  DOI：

  10.1021/jm00088a011
• 作为产物：
  描述：

  N-(t-butoxycarbonyl)glycyl i-butyl carbonate 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -10.0~25.5 ℃ 、355.77 kPa 条件下， 反应 3.5h， 生成 (Pyrrolidin-3-ylcarbamoylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity

  摘要：

  A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3-quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparatively solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S-(R*,R*)]-7-[3-[2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).

  DOI：

  10.1021/jm00088a011

文献信息

• Method for producing aminopyrrolidine derivatives and intermediate compounds
  申请人：Takeyasu Takumi

  公开号：US20070073064A1

  公开（公告）日：2007-03-29

  There is provided an industrial production method of an aminopyrrolidine derivative having chemokine receptor antagonist activity represented by the following formula, a synthetic intermediate thereof and a production method thereof: wherein R 11 is H, C 1 -C 6 alkyl or C 2 -C 7 alkanoyl; R 12 , R 14 , R 15 , R 16 and R 17 are H, halogen, optionally halogenated C 1 -C 6 alkyl, optionally halogenated C 1 -C 6 alkoxy, hydroxyl or C 2 -C 7 alkoxycarbonyl; R 23 , R 24 , R 25 and R 26 are H, halogen, optionally halogenated C 1 -C 6 alkyl, optionally halogenated C 1 -C 6 alkoxy or hydroxyl; and R 3 is H or C 1 -C 6 alkyl.

  提供一种工业生产方法，用于制备化学受体拮抗剂活性的氨基吡咯烷衍生物，其化学式如下，以及其合成中间体和生产方法：其中，R11为H、C1-C6烷基或C2-C7酰基；R12、R14、R15、R16和R17为H、卤素、可选卤代C1-C6烷基、可选卤代C1-C6烷氧基、羟基或C2-C7烷氧羰基；R23、R24、R25和R26为H、卤素、可选卤代C1-C6烷基、可选卤代C1-C6烷氧基或羟基；R3为H或C1-C6烷基。
• PROCESS FOR PRODUCING AMINOPYRROLIDINE DERIVATIVE AND INTERMEDIATE COMPOUND
  申请人：Teijin Pharma Limited

  公开号：EP1676837A1

  公开（公告）日：2006-07-05

  There is provided an industrial production method of an aminopyrrolidine derivative having chemokine receptor antagonist activity represented by the following formula, a synthetic intermediate thereof and a production method thereof: wherein R11 is H, C1-C6 alkyl or C2-C7 alkanoyl; R12, R14, R15, R16 and R17 are H, halogen, optionally halogenated C1-C6 alkyl, optionally halogenated C1-C6 alkoxy, hydroxyl or C2-C7 alkoxycarbonyl; R23, R24, R25 and R26 are H, halogen, optionally halogenated C1-C6 alkyl, optionally halogenated C1-C6 alkoxy or hydroxyl; and R3 is H or C1-C6 alkyl.

  本发明提供了一种具有下式所代表的趋化因子受体拮抗剂活性的氨基吡咯烷衍生物、其合成中间体及其生产方法的工业化生产方法： 其中R11是H、C1-C6烷基或C2-C7烷酰基；R12、R14、R15、R16和R17是H、卤素、任选卤化的C1-C6烷基、任选卤化的C1-C6烷氧基、羟基或C2-C7烷氧基羰基；R23、R24、R25和R26是H、卤素、任选卤化的C1-C6烷基、任选卤化的C1-C6烷氧基或羟基；以及R3是H或C1-C6烷基。
• Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity
  作者：Joseph P. Sanchez、John M. Domagala、Carl L. Heifetz、Stephen R. Priebe、Josephine A. Sesnie、Ashok K. Trehan

  DOI：10.1021/jm00088a011

  日期：1992.5

  A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3-quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3-quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparatively solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S-(R*,R*)]-7-[3-[2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).