JTT-705
CETP抑制剂Chemical Name: 2-Methylpropanethioic acid S-[2-[1-(2-ethylbutyl)cyclohexylcarboxamido]phenyl] ester
CAS No. 211513-37-0
项目整合开发状态: Phase II
项目研究机构: Japan Tobacco (Originator), Roche (Licensee)
合成路线:Cyclohexanecarboxylic acid (I) is condensed with 1-bromo-2-ethylbutane (II) by means of lithium diisopropylamide (LDA) (NaH can also be added ) in THF or THF/cyclohexane to afford derivative (III).Treatment of carboxylic acid (III) with oxalyl chloride in CH2Cl2 (a small amount of DMF can be added) yields acid chloride (IV),which is then coupled with bis(2-aminophenyl) disulfide (V) in pyridine to provide disulfide derivative (VI).Reduction of the disulfide bond of (VI) with PPh3 in dioxane/H2O gives benzenethiol (VII),which is finally coupled with isobutyryl chloride (VIII) in pyridine/CHCl3 to furnish the target compound.
📌 参考资料/链接：
参考文献标题:CEPT activity inhibitors
文献作者:Maeda,K.; Okamoto,H.; Shinkai,H.(Japan Tobacco Inc.)
参考来源:EP 1020439; JP 1999049743; JP 1999222428; WO 9835937
📄 详细内容
合成路线:Cyclohexanecarboxylic acid (I) is condensed with 1-bromo-2-ethylbutane (II) by means of lithium diisopropylamide (LDA) (NaH can also be added ) in THF or THF/cyclohexane to afford derivative (III).Treatment of carboxylic acid (III) with oxalyl chloride in CH2Cl2 (a small amount of DMF can be added) yields acid chloride (IV),which is then coupled with bis(2-aminophenyl) disulfide (V) in pyridine to provide disulfide derivative (VI).Reduction of the disulfide bond of (VI) with PPh3 in dioxane/H2O gives benzenethiol (VII),which is finally coupled with isobutyryl chloride (VIII) in pyridine/CHCl3 to furnish the target compound.
参考文献标题:Bis(2-(acylamino)phenyl) disulfides,2-(acylamino)benzenethiols,and S-(2-(acylamino)phenyl) alkanethioates as novel inhibitors of cholesteryl ester transfer protein
文献作者:Shinkai,H.; Maeda,K.; Yamasaki,T.; Okamoto,H.; Uchida,I.
参考来源:J Med Chem 2000,43(19),3566
产品链接: CAS No. 211513-37-0››