CGS-34225

Chemical Name: N-[1-[2(S)-(Acetylsulfanyl)pentanamido]cyclopent-1-ylcarbonyl]-4-phenyl-L-phenylalanine methyl ester
CAS No. 248262-98-8
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator)
合成路线:Cycloleucine (I) is esterified with HCl/MeOH,and the resultant amino ester (II) is further protected as the tert-butyl carbamate (III) employing Boc2O and Et3N in CH2Cl2.Then,hydrolysis of the methyl ester group of (III) with LiOH furnishes N-Boc-cycloleucine (IV).N-Boc-L-Biphenylalanine (V) is simultaneously deprotected and esterified with HCl/MeOH to yield amino ester (VI).Coupling between N-Boc-cycloleucine (IV) and L-biphenylalanine methyl ester (VI) in the presence of EDC/HOAt gives rise to the protected dipeptide (VII).Subsequent removal of the N-Boc group of (VII) under acidic conditions yields the dipeptide methyl ester (VIII).

合成路线:Diazotization of (R)-2-aminopentanoic acid (IX) in the presence of HBr/KBr gives rise to the configuration-retained alpha-bromoacid (X).This is further coupled to the dipeptide ester (VIII) in the presence of EDC/HOAt to furnish the corresponding alpha-bromo amide (XI).Finally,displacement of the bromide group of (XI) with potassium thioacetate in DMF leads to the target thioacetate ester.