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【结 构 式】 
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【分子编号】52100 【品名】2-(1,3-benzoxazol-2-yl)tetrahydro-2-furancarboxylic acid 【CA登记号】 |
【 分 子 式 】C12H11NO4 【 分 子 量 】233.22368 【元素组成】C 61.8% H 4.75% N 6.01% O 27.44% |
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：(XI)Coupling of 2-tetrahydrofuroic acid (VI) with ortho-aminophenol (VII) by means of PyBOP gave the corresponding ortho-hydroxyanilide (VIII), which was cyclized to the benzoxazole (IX) in the presence of DEAD and triphenylphosphine. The lithium derivative of (IX) was acylated with methyl chloroformate to produce the carboxylate ester (X). Acid (XI), generated by basic hydrolysis of ester (X), was then coupled with amino ester (V) to afford amide (XII). The tert-butyl ester group of (XII) was finally cleaved to the title carboxylic acid by treatment with trifluoroacetic acid.
| 【1】 Yang, G.X.; Hagmann, W.K.; Doherty, G.; Chang, L.L.; Delaszlo, S.E. (Merck & Co., Inc.); Heterocycle amides as cell adhesion inhibitors. WO 0112183 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 52095 | tert-butyl (2S)-2-amino-3-(2',6'-dimethoxy[1,1'-biphenyl]-4-yl)propanoate | C21H27NO4 | 详情 | 详情 | |
| (VI) | 52096 | Tetrahydrofuran-2-carboxylic Acid; 2-Tetrahydrofuroic acid | 16874-33-2 | C5H8O3 | 详情 | 详情 |
| (VII) | 18663 | o-aminophenol; 2-aminophenol | 95-55-6 | C6H7NO | 详情 | 详情 |
| (VIII) | 52097 | N-(2-hydroxyphenyl)tetrahydro-2-furancarboxamide | C11H13NO3 | 详情 | 详情 | |
| (IX) | 52098 | 2-tetrahydro-2-furanyl-1,3-benzoxazole | C11H11NO2 | 详情 | 详情 | |
| (X) | 52099 | methyl 2-(1,3-benzoxazol-2-yl)tetrahydro-2-furancarboxylate | C13H13NO4 | 详情 | 详情 | |
| (XI) | 52100 | 2-(1,3-benzoxazol-2-yl)tetrahydro-2-furancarboxylic acid | C12H11NO4 | 详情 | 详情 | |
| (XII) | 52101 | tert-butyl (2S)-2-([[2-(1,3-benzoxazol-2-yl)tetrahydro-2-furanyl]carbonyl]amino)-3-(2',6'-dimethoxy[1,1'-biphenyl]-4-yl)propanoate | C33H36N2O7 | 详情 | 详情 |
Extended Information