CRL-42796

Chemical Name: N-[4-(4-Piperidinyl)-2-[2-(4-piperidinyl)ethyl]butyryl]glycyl-2(S)-(naphthalen-2-ylsulfonyl)-beta-alanine dihydrochloride
CAS No. 255879-67-5, 255880-36-5 (diHCl)
项目整合开发状态: Preclinical
项目研究机构: Lafon (Originator)
合成路线:Condensation of 4-vinylpyridine (I) with diethyl malonate (II) affords the bis(pyridylethyl)malonate (III) which,upon acidic hydrolysis and decarboxylation leads to mono-acid (IV).Catalytic hydrogenation of the pyridine rings of (IV) in the presence of Pd/C furnishes the corresponding piperidinyl compound (V),which is further protected as the N-Boc derivative (VI) employing di-t-butyl dicarbonate.Acid (VI) is coupled to glycine methyl ester (VII) via activation with cyanuric fluoride to yield amide (VIII).Then,alkaline hydrolysis of the methyl ester group provides carboxylic acid (IX).

合成路线:After activation of acid (IX) as the mixed anhydride with isobutyl chloroformate,coupling with the mono-protected diaminopropionate (X) leads to amide (XI).Subsequent removal of the N-carbobenzoxy group by catalytic hydrogenolysis gives amino ester (XII).This is then acylated by 2-naphthalenesulfonyl chloride (XIII),yielding sulfonamide (XIV).

合成路线:Hydrolysis of ethyl ester (XIV) employing LiOH affords the carboxylic acid (XV).The N-Boc protecting groups are finally removed by treatment with HCl in EtOAc to provide the title compound.