methyl 4-{4-[(methylsulfonyl)amino]phenyl}-4-oxobutanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-{4-[(methylsulfonyl)amino]phenyl}-4-oxobutanoate
• 英文别名: Methyl 4-(4-(methylsulfonamido)phenyl)-4-oxobutanoate；methyl 4-[4-(methanesulfonamido)phenyl]-4-oxobutanoate
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: WGUATYIQDOSEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-{4-[(methylsulfonyl)amino]phenyl}-4-oxobutanoate 在 (-)-B-chlorodiisopinocampheylborane 作用下， 以 四氢呋喃 为溶剂， 以92.1%的产率得到methyl (4S)-4-hydroxy-4-{4-[(methylsulfonyl)amino]phenyl}butanoate
  参考文献：
  名称：

  Chemistry Development of a Convergent Route to Trecetilide Hemi-Fumarate

  摘要：

  A novel, efficient, stereoselective synthetic route for N-(4-{4-[ethyl(6-fluoro -6-methylheptyl)amino]-1-(S)-hyd roxybutyl}-phenyl)methanesulfonamide hemi-fumaric acid salt (trecetilide hemi-fumarate, Figure 1) has been developed. The process features a convergent approach, which assembles two key intermediates in the last step to form the final molecule, which is then isolated by pH-controlled extraction. The new route offers significant yield and purity advantages over the previous route. However, the solvent volume and cycle time were not fully optimized due to the termination of the project.

  DOI：

  10.1021/op049799f
• 作为产物：
  描述：

  甲醇 、 4-[(4-甲磺酰胺基)苯基]-4-氧代丁酸 在 硫酸 作用下， 反应 4.0h， 以97.3%的产率得到methyl 4-{4-[(methylsulfonyl)amino]phenyl}-4-oxobutanoate
  参考文献：
  名称：

  Chemistry Development of a Convergent Route to Trecetilide Hemi-Fumarate

  摘要：

  A novel, efficient, stereoselective synthetic route for N-(4-{4-[ethyl(6-fluoro -6-methylheptyl)amino]-1-(S)-hyd roxybutyl}-phenyl)methanesulfonamide hemi-fumaric acid salt (trecetilide hemi-fumarate, Figure 1) has been developed. The process features a convergent approach, which assembles two key intermediates in the last step to form the final molecule, which is then isolated by pH-controlled extraction. The new route offers significant yield and purity advantages over the previous route. However, the solvent volume and cycle time were not fully optimized due to the termination of the project.

  DOI：

  10.1021/op049799f

文献信息

• Compounds and methods for preparing methanesulfonamides
  申请人：MacKey Suzanne Sonja

  公开号：US20050148796A1

  公开（公告）日：2005-07-07

  A process for preparing (S)-(−)-N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxylphenyl]methanesulfonamide hemifumarate salt, which comprises reacting N-[4-[(2S)-tetrahydro-5-hydroxy-2-furanyl]phenyl]methanesulfonamide(IIa) with fluoroamine (III) in the presence of triacetoxyborohydride and ethyl acetate to provide [4-[-4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxylphenyl]methanesulfonamide(I) and then converting I into the hemifumarate salt Ia. A process for preparing IIa is also claimed as well as intermediates IIa-IId.

  一种制备（S）-（-）-N- [4- [4- [乙基（6-氟-6-甲基庚基）氨基] -1-羟基苯基]甲烷磺酰胺半富马酸盐的方法，包括在三乙酰氧硼氢化钠和乙酸乙酯的存在下，将N- [4- [(2S) -四氢-5-羟基-2-呋喃基]苯基]甲烷磺酰胺（IIa）与氟胺（III）反应，以提供[4- [-4- [乙基（6-氟-6-甲基庚基）氨基] -1-羟基苯基]甲烷磺酰胺（I），然后将I转化为半富马酸盐Ia。还声明了制备IIa的方法以及中间体IIa-IId。
• COMPOUNDS AND METHODS FOR PREPARING METHANESULFONAMIDES
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1395549A1

  公开（公告）日：2004-03-10
• US7232930B2
  申请人：——

  公开号：US7232930B2

  公开（公告）日：2007-06-19
• [EN] COMPOUNDS AND METHODS FOR PREPARING METHANESULFONAMIDES<br/>[FR] COMPOSES ET PROCEDES D'ELABORATION DE METHANESULFONAMIDES
  申请人：UPJOHN CO

  公开号：WO2002098845A1

  公开（公告）日：2002-12-12

  A process for preparing (S)-(-)-N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl]methanesulfonamide hemifumarate salt, which comprises reacting N-[4[(2S)-tetrahydro-5-hydroxy-2-furanyl]phenyl]methanesulfonamide (IIa) with fluoroamine (III) in the presence of triacetoxyborohydride and ethyl acetate to provide [4-[-4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxy]phenyl]methanesulfonamide (I) and then converting I into the hemifumarate salt Ia. A process for preparing IIa is also claimed as well as intermediates IIa-IId.
• Chemistry Development of a Convergent Route to Trecetilide Hemi-Fumarate
  作者：Sonja S. Mackey、Haifeng Wu、Michael E. Matison、Michael Goble

  DOI：10.1021/op049799f

  日期：2005.3.1

  A novel, efficient, stereoselective synthetic route for N-(4-4-[ethyl(6-fluoro -6-methylheptyl)amino]-1-(S)-hyd roxybutyl}-phenyl)methanesulfonamide hemi-fumaric acid salt (trecetilide hemi-fumarate, Figure 1) has been developed. The process features a convergent approach, which assembles two key intermediates in the last step to form the final molecule, which is then isolated by pH-controlled extraction. The new route offers significant yield and purity advantages over the previous route. However, the solvent volume and cycle time were not fully optimized due to the termination of the project.