CP-544372

Chemical Name: 9(S)-Amino-9-deoxo-4''-O-[N-[2-[N-ethyl-N-[1(S)-(2-methoxyphenyl)ethyl]amino]ethyl]carbamoyl]erythromycin A
CAS No. 220217-04-9
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:The C-9 amino group of erythromycylamine (I) was protected by reaction with Boc2O to give the corresponding tert-butyl carbamate (II).Subsequent acetylation of the 2'-hydroxyl group of (II) with Ac2O provided acetate (III).Then,condensation of (III) with carbonyldiimidazole at the 4''-hydroxyl group afforded the acyl imidazole (IV).The chiral diamine (VIII) was synthesized by reductive condensation of 2-phthalimido acetaldehyde (V) with the (S)-phenylethylamine derivative (VI),followed by hydrazinolysis of the resulting phtalimide (VII).Diamine (VIII) was then coupled with acyl imidazole (IV) to afford carbamate (IX).

合成路线:Introduction of an N-ethyl group in (IX) was accomplished by reductive condensation with acetaldehyde and NaBH(OAc)3 to give (X).The Boc group of (X) was deprotected by treatment with trimethylsilyl triflate and 2,6-lutidine,and then reaction of the resulting silyl ether with tetrabutylammonium fluoride in THF yielding (XI).Finally,the 2'-acetyl group of (XI) was removed by treatment with methanol.