新产品编号:1968517

Chemical Name: N-[3-Methyl-1(S)-[N-[4-oxotetrahydrofuran-3(S)-yl]carbamoyl]butyl]benzothiophene-2-carboxamide; N2-(Benzothien-2-ylcarbonyl)-N1-[4-oxotetrahydrofuran-3(S)-yl]-L-leucinamide
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Asymmetric opening of epoxide (I) with trimethylsilyl azide in the presence of (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-chromium as the chiral catalyst (Salen catalyst) provided the (3S,4R)-azido silyl alcohol (II).Removal of the silyl group with camphorsulfonic acid in MeOH and subsequent reduction of the azido moiety of (II) with hydrogen in the presence of Pd/C afforded the amino alcohol (III).Coupling of (III) with the mixed anhydride prepared from N-Cbz-leucine (IV) and isobutyric acid gave amide (V).The N-carbobenzoxy group of (V) was then removed by hydrogenolysis,yielding amine (VI),which was coupled with benzothiophene-2-carbonyl chloride (VII) to furnish the diamide (VIII).The secondary alcohol of (VIII) was finally oxidized to the target ketone using the Dess-Martin reagent in CH2Cl2.