tert-butyl N-[2-[[(2R)-3-(4-cyanophenyl)-1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamate | 835917-11-8

• 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: tert-butyl N-[2-[[(2R)-3-(4-cyanophenyl)-1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 835917-11-8
• 化学式: C₂₄H₂₆Cl₂N₄O₄
• 分子量: 505.401
• InChiKey: GSILZIKNICHLLJ-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[[(2R)-3-(4-cyanophenyl)-1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamate 在 三甲基氯硅烷 、 Celite 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 sodium iodide 、 copper(l) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 0.83h， 生成 (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one
  参考文献：
  名称：

  A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of thiohydantoins

  摘要：

  An efficient and chromatography-free approach for synthesis of a new class of LFA- I inhibitor was developed. A copper(I) chloride-promoted intramolecular cyclization of thiohydantoins 7a-b serves as a key step to highly functionalized bicyclic guanidines 5a-b, that were subsequently converted to H-imidazol[l,2-a]imidazol-2-one LFA-1 inhibitors. This process has been successfully implemented in the pilot plant to produce multikilogram quantities of LFA-1 inhibitors such as la-b. (C) 2004 Elsevier Ltd. All ri.-hts reserved

  DOI：

  10.1016/j.tetlet.2004.11.065
• 作为产物：
  描述：

  (2R,5R)-3-(3,5-二氯苯基)-2-异丙基-5-甲基-1-(2,2,2-三氯乙酰基)-咪唑烷-4-酮 在 sodium hydroxide 、 三甲基乙酰氯 、 苄基三甲基氢氧化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 tert-butyl N-[2-[[(2R)-3-(4-cyanophenyl)-1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of thiohydantoins

  摘要：

  An efficient and chromatography-free approach for synthesis of a new class of LFA- I inhibitor was developed. A copper(I) chloride-promoted intramolecular cyclization of thiohydantoins 7a-b serves as a key step to highly functionalized bicyclic guanidines 5a-b, that were subsequently converted to H-imidazol[l,2-a]imidazol-2-one LFA-1 inhibitors. This process has been successfully implemented in the pilot plant to produce multikilogram quantities of LFA-1 inhibitors such as la-b. (C) 2004 Elsevier Ltd. All ri.-hts reserved

  DOI：

  10.1016/j.tetlet.2004.11.065

文献信息

• A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of thiohydantoins
  作者：Xiao-jun Wang、Li Zhang、Yibo Xu、Dhileepkumar Krishnamurthy、Richard Varsolona、Laurence Nummy、Sherry Shen、Rogelio P. Frutos、Denis Byrne、J.C. Chung、Vittorio Farina、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2004.11.065

  日期：2005.1

  An efficient and chromatography-free approach for synthesis of a new class of LFA- I inhibitor was developed. A copper(I) chloride-promoted intramolecular cyclization of thiohydantoins 7a-b serves as a key step to highly functionalized bicyclic guanidines 5a-b, that were subsequently converted to H-imidazol[l,2-a]imidazol-2-one LFA-1 inhibitors. This process has been successfully implemented in the pilot plant to produce multikilogram quantities of LFA-1 inhibitors such as la-b. (C) 2004 Elsevier Ltd. All ri.-hts reserved