LY-195448
Chemical Name: (R)-4-[3-[(2-Hydroxy-2-phenylethyl)amino]-3-methylbutyl]benzamide
CAS No. 74249-21-1 (monoHCl, no stereoch.), 74249-20-0 (undefined stereoch.)
项目整合开发状态: Phase I
项目研究机构: Lilly (Originator)
合成路线:The reaction of 4-(3-hydroxy-3-methylbutyl)benzoic acid (I) with HCN in acetic acid-H2SO4 gives 4-[3-(formylamino)-3-methyibutylbenzoic acid (II),which is hydrolyzed to the corresponding amine (III) with aqueous HCl at 100 C.The reaction of benzoic acid (III) with SOCl2 gives the corresponding acyl chloride (IV),which by reaction with NH3 is converted to the benzamide (V).Finally,this compound is condensed with styrene oxide (VI) by means of hexamethyldisylazane in DMSO and hydrolyzed with NaOH in butanone water.
📌 参考资料/链接：
参考文献标题:Phenethanolamines,their formulations,preparation
文献作者:Mills,J.; Schmiegel,K.K.; Toomey,R.E.(Eli Lilly and Company)
参考来源:EP 0007206
📄 详细内容
合成路线:The reaction of 4-(3-hydroxy-3-methylbutyl)benzoic acid (I) with HCN in acetic acid-H2SO4 gives 4-[3-(formylamino)-3-methyibutylbenzoic acid (II),which is hydrolyzed to the corresponding amine (III) with aqueous HCl at 100 C.The reaction of benzoic acid (III) with SOCl2 gives the corresponding acyl chloride (IV),which by reaction with NH3 is converted to the benzamide (V).Finally,this compound is condensed with styrene oxide (VI) by means of hexamethyldisylazane in DMSO and hydrolyzed with NaOH in butanone water.
参考文献标题:Process for preparing 2-hydroxy-2-phenethylamines
文献作者:Weigel,L.O.(Eli Lilly and Company)
参考来源:EP 0104888
合成路线:The reaction of 4-(3-hydroxy-3-methylbutyl)benzoic acid (I) with HCN in acetic acid-H2SO4 gives 4-[3-(formylamino)-3-methyibutylbenzoic acid (II),which is hydrolyzed to the corresponding amine (III) with aqueous HCl at 100 C.The reaction of benzoic acid (III) with SOCl2 gives the corresponding acyl chloride (IV),which by reaction with NH3 is converted to the benzamide (V).Finally,this compound is condensed with styrene oxide (VI) by means of hexamethyldisylazane in DMSO and hydrolyzed with NaOH in butanone water.
参考文献标题:LY-195448
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1988,13(12),1045