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【结 构 式】 
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【分子编号】20753 【品名】1-[2-(tert-butoxycarbonyl)-4-phenylbutyl]cyclopentanecarboxylic acid 【CA登记号】 |
【 分 子 式 】C21H30O4 【 分 子 量 】346.4668 【元素组成】C 72.8% H 8.73% O 18.47% |
合成路线1
该中间体在本合成路线中的序号：rac-(II)2b) The alkylation of 2-(dimethoxyphosphoryl)acetic acid tert-butyl ester (XII) with 2-phenylethyl bromide (XIII) by means of potassium tert-butoxide in DMF gives 2-(dimethoxyphosphoryl)-4-phenylbutyric acid tert-butyl ester (XIV), which is allowed to react with formaldehyde/potasium tert-butoxide in THF to afford the tert-butyl acrylate (XV). The condensation of (XV) with cyclopentanecarboxylic acid (XVI) by means of butyllithium/diisopropylamine in THF affords racemic (II), which is finally submitted to optical resolution with L-(-)-alpha-methylbenzylamine to afford the chiral (R)-intermediate (II).
| 【1】 Rozsa, S.; Gy Papp, J.; Thormahlen, D.; Waldeck, H. (Solvay SA); Drugs for increasing gastrointestinal blood supply. DE 19638020; EP 0830863; JP 1998101565 . |
| 【2】 Waldeck, H.; Höltje, D.; Messinger, J.; Antel, J.; Wurl, M.; Thormählen, D. (Kali-Chemie AG); Benzazepin-, benzoxazepin- and benzothiazepin-N-acetic acid-derivs., their preparation and their pharmaceutical compsns.. CA 2172354; EP 0733642; JP 1996269011; US 5677297 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| rac-(II) | 20753 | 1-[2-(tert-butoxycarbonyl)-4-phenylbutyl]cyclopentanecarboxylic acid | C21H30O4 | 详情 | 详情 | |
| (XII) | 20748 | tert-butyl 2-(dimethoxyphosphoryl)acetate | C8H17O5P | 详情 | 详情 | |
| (XIII) | 20730 | 1-(2-bromoethyl)benzene；1-Bromo-2-phenylethane;(2-Bromoethyl)benzene;Phenethyl bromide | 103-63-9 | C8H9Br | 详情 | 详情 |
| (XIV) | 20750 | tert-butyl 2-(dimethoxyphosphoryl)-4-phenylbutanoate | C16H25O5P | 详情 | 详情 | |
| (XV) | 20751 | tert-butyl 2-phenethylacrylate | C15H20O2 | 详情 | 详情 | |
| (XVI) | 20734 | cyclopentanecarboxylic acid | 3400-45-1 | C6H10O2 | 详情 | 详情 |