新产品编号:1383177

Chemical Name: 6-Aza-3-oxoandrost-4-en-17-beta-carboxylic acid methyl ester
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Treatment of the 3b-hydroxyetienic acid derivative (I) with nitrosylsulfuric acid in Et2O produced the enone 5,6-seconitrile (III) through a Beckmann fragmentation of the intermediate a-hydroxy oxime (II) and subsequent b-elimination.Enone (III) was epoxidized with H2O2 and NaOH to produce epoxyketone (IV),which was rearranged to diketone (V) using tetrakis(triphenylphosphine)-palladium and 1,2-bis(diphenylphosphine)ethane as the catalysts.The nitrile group of (V) was subsequently hydrolyzed to amide with HCl in MeOH-Et2O at 0 C,with concurrent transformation to the enol ether (VI),which was accompanied by its vinylogous ester isomer.Then,a tandem Hoffmann rearrangement-cyclocondensation reaction upon treating with hydroxy(tosyloxy)iodobenzene afforded the 6-azasteroid.