【药物名称】CP-544372
化学结构式(Chemical Structure):
参考文献No.483445
标题:Novel erythromycylamine 4-carbamate antibacterial agents: Synthesis and biological evaluation resulting in discovery of CP-544372
作者:Girard, A.E.; Cimochoski, C.R.; Brennan, L.A.; Smyth, K.T.; Duignan, J.M.; Finegan, S.M.; Kaneko, T.; Su, W.G.; Sutcliffe, J.A.; Rainville, J.P.
来源:38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998,Abst F-122
合成路线图解说明:

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).

合成路线图解说明:

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.

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