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【结 构 式】 
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【分子编号】38807 【品名】methyl 2-(4-methoxyphenyl)-2-(4-nitro-1H-imidazol-1-yl)acetate 【CA登记号】 |
【 分 子 式 】C13H13N3O5 【 分 子 量 】291.26344 【元素组成】C 53.61% H 4.5% N 14.43% O 27.47% |
合成路线1
该中间体在本合成路线中的序号：(XI)4-Methoxyphenylacetic acid (VII) was esterified with EtOH and p-toluenesulfonic acid. The resulting ethyl ester (VIII) was brominated by means of N-bromosuccinimide to produce bromoester (IX), which was condensed with 4-nitroimidazole (X) yielding (XI). Reduction of the nitro group of (XI) by catalytic hydrogenation over Pd/C gave amine (XII). This was coupled with acid (VI) by means of EDC and HOBt to afford amide (XIII). Then, hydrolysis of the methyl ester of (XIII) with LiOH gave rise to carboxylic acid (XIV). Finally, coupling of (XIV) with 4-methylpiperidine (XV) generated the title compound.
| 【1】 Growth hormone secretagogues. EP 0933365; WO 9908699 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 28103 | (2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propionic acid | C19H28N2O6 | 详情 | 详情 | |
| (VII) | 34793 | 2-(4-methoxyphenyl)acetic acid; p-Methoxyphenyl formate; Homoanisic acid; p-Methyl benzyl formate; 4-methoxyphenylacetic acid; 4-methoxybenzeneacetic acid; p-methoxyphenylacetic acid | 104-01-8 | C9H10O3 | 详情 | 详情 |
| (VIII) | 38805 | methyl 2-(4-methoxyphenyl)acetate | 23786-14-3 | C10H12O3 | 详情 | 详情 |
| (IX) | 38806 | methyl 2-bromo-2-(4-methoxyphenyl)acetate | C10H11BrO3 | 详情 | 详情 | |
| (X) | 35764 | 4-nitro-1H-imidazole | 3034-38-6 | C3H3N3O2 | 详情 | 详情 |
| (XI) | 38807 | methyl 2-(4-methoxyphenyl)-2-(4-nitro-1H-imidazol-1-yl)acetate | C13H13N3O5 | 详情 | 详情 | |
| (XII) | 38808 | methyl 2-(4-amino-1H-imidazol-1-yl)-2-(4-methoxyphenyl)acetate | C13H15N3O3 | 详情 | 详情 | |
| (XIII) | 38809 | methyl 2-(4-[[(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoyl]amino]-1H-imidazol-1-yl)-2-(4-methoxyphenyl)acetate | C32H41N5O8 | 详情 | 详情 | |
| (XIV) | 38810 | 2-(4-[[(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoyl]amino]-1H-imidazol-1-yl)-2-(4-methoxyphenyl)acetic acid | C31H39N5O8 | 详情 | 详情 | |
| (XV) | 10192 | 4-Methylpiperidine; gamma-Pipecoline | 626-58-4 | C6H13N | 详情 | 详情 |