(1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester | 769167-58-0

• 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: (1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester
• 英文别名: 1-{[4-(4-bromobenzenesulfonyloxy)-1-(2-cyclopentyloxycarbonylamino-non-8-enoyl)pyrrolidine-2-carbonyl]amino}-2-vinyl-cyclopropanecarboxylic acid methyl ester；BILN1；methyl (1R,2S)-1-[[(2S,4S)-4-(4-bromophenyl)sulfonyloxy-1-[(2S)-2-(cyclopentyloxycarbonylamino)non-8-enoyl]pyrrolidine-2-carbonyl]amino]-2-ethenylcyclopropane-1-carboxylate
• CAS: 769167-58-0
• 化学式: C₃₃H₄₄BrN₃O₉S
• 分子量: 738.697
• InChiKey: WQGMRNRJGJAJCY-ISMBVHEDSA-N

物化性质

• 沸点：
  863.3±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester 在 dichloro(o-isporopoxyphenylmethylene)(triphenylphosphine)ruthenium(II) N-甲基吡咯烷酮 、 2-巯基烟酸 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 (1S,4R,6S,7Z,14S,18R)-14-cyclopentyloxycarbonylamino-18-[2-(2-isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-7-ene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Efficient Large-Scale Synthesis of BILN 2061, a Potent HCV Protease Inhibitor, by a Convergent Approach Based on Ring-Closing Metathesis

  摘要：

  A multistep scalable synthesis of the clinically important hepatitis C virus (HCV) protease inhibitor BILN 2061 (1) is described. The synthesis is highly convergent and consists of two amide bond formations, one etherification, and one ring-closing metathesis (RCM) step, using readily available building blocks 2-5. The optimization of each step is described at length. The main focus of the paper is the study of the RCM step and the description of the main problems faced when scaling up to pilot scale this highly powerful but very challenging synthetic operation. Eventually, the RCM reaction was smoothly scaled up to produce > 400 kg of cyclized product.

  DOI：

  10.1021/jo060285j
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在