【结 构 式】 |
【分子编号】57502 【品名】benzyl 5-formyl-2-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C16H14O4 【 分 子 量 】270.28476 【元素组成】C 71.1% H 5.22% O 23.68% |
合成路线1
该中间体在本合成路线中的序号:(II)5-Formyl-2-methoxybenzoic acid (I) is converted to the corresponding benzyl ester (II) upon treatment with benzyl bromide and potassium bicarbonate. Subsequent Wadsworth-Emmons condensation between aldehyde (II) and triethyl 2-phosphonobutyrate (III) gives the unsaturated ester (IV). Double bond hydrogenation in (IV) with concomitant hydrogenolysis of the benzyl ester affords acid (V), which is subsequently coupled with 4-(trifluoromethyl)benzyl amine (VI), via the mixed anhydride with ethyl chloroformate, to produce amide (VII). The ethyl ester group of (VII) is finally hydrolyzed to the title carboxylic acid employing NaOH in aqueous ethanol.
【1】 Tanase, T.; Nomura, M.; Miyachi, H.; et al.; Design, synthesis and evaluation of substituted phenylpropanoic acid derivatives as peroxisome proliferator-activated receptor (PPAR) activators: Novel human PPARalpha-selective activators. Bioorg Med Chem Lett 2002, 12, 1, 77. |
【2】 Murakami, K.; Takahashi, Y.; Nomura, M.; Miyachi, H.; Ide, T.; Tsunoda, M.; Tanase, T. (Kyorin Pharmaceutical Co., Ltd.); Substd. phenylpropionic acid derivs. as agonists to human peroxisome proliferator-activated receptor (PPAR) alpha. EP 1184366; JP 2001055367; WO 0075103 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 57501 | 5-formyl-2-methoxybenzoic acid | C9H8O4 | 详情 | 详情 | |
(II) | 57502 | benzyl 5-formyl-2-methoxybenzoate | C16H14O4 | 详情 | 详情 | |
(III) | 20274 | ethyl 2-(diethoxyphosphoryl)butanoate | 17145-91-4 | C10H21O5P | 详情 | 详情 |
(IV) | 57503 | benzyl 5-[(E)-2-(ethoxycarbonyl)-1-butenyl]-2-methoxybenzoate | C22H24O5 | 详情 | 详情 | |
(V) | 57504 | 5-[2-(ethoxycarbonyl)butyl]-2-methoxybenzoic acid | C15H20O5 | 详情 | 详情 | |
(VI) | 21925 | [4-(trifluoromethyl)phenyl]methanamine; 4-(trifluoromethyl)benzylamine | 3300-51-4 | C8H8F3N | 详情 | 详情 |
(VII) | 57505 | ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)benzyl]butanoate | C23H26F3NO4 | 详情 | 详情 |