A-177775

Chemical Name: 3'-N-Cyclopentyl-3'-N-demethyl-11-deoxy-11-[2-(3,4-dichlorophenyl)ethylamino]-6-O-methylerythromycin A 11-N,12-O-(cyclic carbamate)
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:6-O-Methylerythromycin A (I) was protected as the 2'-acetate (II) and subsequently treated with chlorotrimethylsilane and pyridine to afford the 4''-O-silyl ether (III).Condensation of (III) with 1,1'-carbonyldiimidazole yielded the 12-O-acylimidazole derivative (IV),which was subsequently reacted with 3,4-dichlorophenethyl amine (V) to form the 11,12-cyclic carbamate (VI).Deprotection of the acetate ester of (VI) on heating with methanol,followed by desilylation with tetrabutylammonium fluoride in THF yielded (VII).

合成路线:N-Demethylation by treatment with iodine and sodium acetate under irradiation of a halogen lamp produced secondary amine (VIII).Finally,reductive condensation of (VIII) with cyclopentanone (IX) in the presence of sodium cyanoborohydride yielded the title cyclopentylamino compound.