新产品编号:1596747

Chemical Name: 3',3'-N-Bis(cyclopropylmethyl)-3',3'-N-bis(desmethyl)-11-[2-(3-chloro-4-fluorophenyl)ethylamino]-11-deoxy-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-chloro-4-fluorophenethyl 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:Treatment of (VII) with iodine and sodium acetate under irradiation of a halogen lamp produced N-demethylation to furnish (VIII).Further demethylation of (VIII) to give (IX) was achieved by a similar treatment with iodine and tripotassium phosphate.Finally,reductive condensation of (IX) with cyclopropanecarbaldehyde (X) in the presence of sodium cyanoborohydride yielded the bis(cyclopropylmethyl) derivative.