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【结 构 式】

【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%

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: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
Extended Information