新产品编号:225153

Chemical Name: N-[1(S)-[3-(N-Benzyloxycarbonyl-L-leucylamino)-4-oxopyrrolidin-1-ylcarbonyl]-3-methylbutyl]carbamic acid benzyl ester
CAS No. 190141-90-3
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:3-Pyrroline (I) was protected with di-tert-buyl dicarbonate to give N-Boc-pyrroline (II),which was then epoxidized with meta-chloroperbenzoic acid.The resulting epoxide (III) was opened with sodium azide in aqueous MeOH to yield trans-azidoalcohol (IV).Subsequent reduction of the azide (IV) to aminoalcohol (V) was effected by hydrogenation over Pd/C (1).Condensation of the racemic trans-aminoalcohol (V) with N-Cbz-L-leucine (VI) in the presence of EDC and HOBt provided amide (VII) as a diastereomeric mixture.The N-Boc group of (VII) was then deprotected with HCl in EtOAc,and the resulting amine (VIII) was coupled with another N-Cbz-L-leucine (VI) unit to give (IX).Oxidation of the alcohol group of (IX) to the target ketone was accomplished with Jones reagent in acetone.The diastereomeric mixture was separated by reverse phase-HPLC,however the diastereomers were not configurationally stable and reequilibrated spontaneusly to the original mixture.