2-(4-[[(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoyl]amino]-1H-imidazol-1-yl)-2-(4-methoxyphenyl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】38810

【品名】2-(4-[[(2R)-3-(benzyloxy)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)propanoyl]amino]-1H-imidazol-1-yl)-2-(4-methoxyphenyl)acetic acid

【CA登记号】

【分子式】C₃₁H₃₉N₅O₈

【分子量】609.67956

【元素组成】C 61.07% H 6.45% N 11.49% O 20.99%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XIV)

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.

参考文献中间体

合成目标

【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

Extended Information