methyl 3-(6-ethylsulfonylpyridin-3-yl)oxy-5-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxybenzoate | 1137917-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(6-ethylsulfonylpyridin-3-yl)oxy-5-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxybenzoate
• CAS: 1137917-07-7
• 化学式: C₂₇H₄₁NO₇SSi
• 分子量: 551.777
• InChiKey: MYCLHSRAZMHHJJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-(6-ethylsulfonylpyridin-3-yl)oxy-5-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxybenzoate 在 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  A Large-Scale Synthesis of Potent Glucokinase Activator MK-0941 via Selective O-Arylation and O-Alkylation

  摘要：

  An efficient, practical preparation of MK-0941, a potent glucokinase activator, is described. Keys to the success of the synthesis are a highly selective mono-O-arylation of methyl 3,5-dihydroxybenzoate with 2-ethanesulfonyl-5-chloropyridine and the choice of a proper protective group for the subsequent S(N)2 O-alkylation. With the thorough understanding of the origins and fate of in-process impurities, the second-generation robust synthesis with a minimum number of operations reproducibly prepares MK-0941 in 56% overall yield with >99% purity.

  DOI：

  10.1021/op200068c
• 作为产物：
  描述：

  5-氯-2-(乙基磺酰基)吡啶 在 potassium tert-butylate 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 methyl 3-(6-ethylsulfonylpyridin-3-yl)oxy-5-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]oxybenzoate
  参考文献：
  名称：

  A Large-Scale Synthesis of Potent Glucokinase Activator MK-0941 via Selective O-Arylation and O-Alkylation

  摘要：

  An efficient, practical preparation of MK-0941, a potent glucokinase activator, is described. Keys to the success of the synthesis are a highly selective mono-O-arylation of methyl 3,5-dihydroxybenzoate with 2-ethanesulfonyl-5-chloropyridine and the choice of a proper protective group for the subsequent S(N)2 O-alkylation. With the thorough understanding of the origins and fate of in-process impurities, the second-generation robust synthesis with a minimum number of operations reproducibly prepares MK-0941 in 56% overall yield with >99% purity.

  DOI：

  10.1021/op200068c

文献信息

• METHOD FOR PRODUCING PYRAZOL-3-YL-BENZAMIDE DERIVATIVE
  申请人：Asakawa Kenichi

  公开号：US20100222394A1

  公开（公告）日：2010-09-02

  The present invention provides a more efficient industrial method for producing a pyrazol-3-yl-benzamide derivative expressed by a formula useful as medicine: wherein R 2 , R 3 and R 4 each independently represent a lower alkyl group.

  本发明提供了一种更有效的工业生产方法，用于生产一种表示为以下公式的作为药物有用的吡唑-3-基苯甲酰胺衍生物： 其中R2、R3和R4分别独立地表示较低的烷基基团。
• Org. Process Res. Dev. 2011, 15, 824-830
  作者：

  DOI：——

  日期：——
• A Large-Scale Synthesis of Potent Glucokinase Activator MK-0941 via Selective <i>O</i>-Arylation and <i>O</i>-Alkylation
  作者：Naoki Yoshikawa、Feng Xu、Juan D. Arredondo、Takahiro Itoh

  DOI：10.1021/op200068c

  日期：2011.7.15

  An efficient, practical preparation of MK-0941, a potent glucokinase activator, is described. Keys to the success of the synthesis are a highly selective mono-O-arylation of methyl 3,5-dihydroxybenzoate with 2-ethanesulfonyl-5-chloropyridine and the choice of a proper protective group for the subsequent S(N)2 O-alkylation. With the thorough understanding of the origins and fate of in-process impurities, the second-generation robust synthesis with a minimum number of operations reproducibly prepares MK-0941 in 56% overall yield with >99% purity.