(1S,4S)-5-((2-nitrophenyl)sulfonyl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one | 1510832-15-1

• 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: (1S,4S)-5-((2-nitrophenyl)sulfonyl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one
• 英文别名: (1S,4S)-5-(2-nitrophenyl)sulfonyl-2-oxa-5-azabicyclo[2.2.2]octan-3-one
• CAS: 1510832-15-1
• 化学式: C₁₂H₁₂N₂O₆S
• 分子量: 312.303
• InChiKey: NXVXWMDWVRBRRO-WPRPVWTQSA-N

物化性质

• 沸点：
  573.0±60.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,4S)-5-((2-nitrophenyl)sulfonyl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one 在 碳酸甲丙酯 、 4-二甲氨基吡啶 、 氢气 、 三氧化硫吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， -18.0~72.0 ℃ 、411.6 kPa 条件下， 反应 35.85h， 生成 硫酸单[(1R,2S,5R)-7-氧代-2-[(4-哌啶基氨基)羰基]-1,6-二氮杂双环[3.2.1]辛-6-基]酯
  参考文献：
  名称：

  Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor

  摘要：

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

  DOI：

  10.1021/ol4031606
• 作为产物：
  描述：

  (2S,5S)-5-羟基哌啶-2-甲酸 在 邻硝基苯磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 生成 (1S,4S)-5-((2-nitrophenyl)sulfonyl)-2-oxa-5-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor

  摘要：

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

  DOI：

  10.1021/ol4031606

文献信息

• PREPARATION OF TERT-BUTYL 4-((1R,2S,5R)-6- (BENZYLOXY)-7-0X0-1,6-DIAZABICYCL0[3.2.I]OCTANE-2- CARBOXAMIDO)PIPERIDINE-1-CARBOXYLATE
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3008069B1

  公开（公告）日：2018-01-03
• PROCESS FOR THE PREPARATION OF CHIRAL TERT-BUTYL 4-((1R,2S,5R)-6-(BENZYLOXY)-7-OXO-1,6-DIAZABICYCLO[3.2.1]OCTANE-2-CARBOXAMIDO)PIPERIDINE-1-CARBOXYLATE DERIVATIVES AND (2S,5R)-7-OXO-N-PIPERIDIN-4-YL-6-(SULFOXY)-1,6-DIAZABICYCLO[3.2.1]OCTANE-2-CARBOXAMIDE
  申请人：MILLER Steven P.

  公开号：US20160122350A1

  公开（公告）日：2016-05-05

  A process for the preparation of N-protected 6-(piperidin-4-ylcarbamoyl)piperidin-3-yl sulfonates of Formula (III): which comprises contacting a lactone of Formula (II): with an azacycloalkylamine of formula (II-Am): followed by contact with a sulfonyl halide of formula (II-Su): R 4 —SO 2 W (II-Su) in the presence of tertiary amine base, wherein P G1 and P G2 are amine protective groups; k, p and q are 0, 1, or 2, and W, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are defined herein. Additional embodiments add a series of process steps leading to the synthesis of 7-oxo-1,6-diazabicyclo[3.2.1]octanes suitable for use as β-lactamase inhibitors.
• US9604985B2
  申请人：——

  公开号：US9604985B2

  公开（公告）日：2017-03-28
• Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor
  作者：Steven P. Miller、Yong-Li Zhong、Zhijian Liu、Michael Simeone、Nobuyoshi Yasuda、John Limanto、Zheng Chen、Joseph Lynch、Vincent Capodanno

  DOI：10.1021/ol4031606

  日期：2014.1.3

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.