Cetamolol hydrochloride, ICI-72222(free base), AI-27303-药物合成数据库

【药物名称】Cetamolol hydrochloride, ICI-72222(free base), AI-27303

化学结构式(Chemical Structure):

参考文献No.	65201
标题:	Cetamolol hydrochloride
作者:	Hillier, K.; Casta馿r, J.; Blancafort, P.; Serradell, M.N.
来源:	Drugs Fut 1983,8(4),305

合成路线图解说明: The condensation of 2-(N-methylcarbamoylmethoxy)phenol (I) with 3-benzyloxy-1-(p-toluenesulfonyloxy)-2-propanol (II) by means of Na in refluxing methoxyethanol gives 3 benzyloxy-1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2-propanol (III), which is debenzylated by hydrogenolysis with H2 over Pd/C in methanol yielding 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-propanediol (IV). The tosylation of (IV) with tosyl chloride in pyridine affords 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-3-tosyloxy-2-propanol (V), which by treatment with NaOH in water is converted into 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-epoxypropane (VI). Finally, this compound is treated with tertbutylamine in refluxing tert-butanol.

参考文献No.	701233
标题:
作者:	Tucker, H.
来源:	FR 2250752

合成路线图解说明: The condensation of 2-(N-methylcarbamoylmethoxy)phenol (I) with 3-benzyloxy-1-(p-toluenesulfonyloxy)-2-propanol (II) by means of Na in refluxing methoxyethanol gives 3 benzyloxy-1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2-propanol (III), which is debenzylated by hydrogenolysis with H2 over Pd/C in methanol yielding 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-propanediol (IV). The tosylation of (IV) with tosyl chloride in pyridine affords 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-3-tosyloxy-2-propanol (V), which by treatment with NaOH in water is converted into 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-epoxypropane (VI). Finally, this compound is treated with tertbutylamine in refluxing tert-butanol.