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【结 构 式】

【分子编号】20731

【品名】diethyl 2-phenethylmalonate

【CA登记号】

【 分 子 式 】C15H20O4

【 分 子 量 】264.3214

【元素组成】C 68.16% H 7.63% O 24.21%

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)

2b) The chiral intermediate acid (II) has been obtained as follows: The alkylation of diethyl malonate (XII) with 2-phenylethyl bromide (XIII) by means of potassium tert-butoxide in DMF gives diethyl 2-(2-phenylethyl)malonate (XIV), which is treated with KOH in ice-cooled water to afford the corresponding monoester monoacid (XV). The reacction of (XV) with formaldehyde in piperidine/water gives teh acrylate (XVI), which is condensed with cyclopentanecarboxylic acid (XVII) by meansof butyllithium/diisopropylamine in THF to afford racemic (II). Finally, this racemate is submitted to optical resolution with L-(-)-alpha-methylbenzylamine to afford the chiral (R)-intermediate (II).

1 Sorbera, L.A.; Leeson, P.A.; Castañer, J.; SLV-306. Drugs Fut 2002, 27, 1, 27.
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 .
3 Rozsa, S.; Gy Papp, J.; Thormahlen, D.; Waldeck, H. (Solvay SA); Drugs for increasing gastrointestinal blood supply. DE 19638020; EP 0830863; JP 1998101565 .
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) 20735 1-[2-(ethoxycarbonyl)-4-phenylbutyl]cyclopentanecarboxylic acid C19H26O4 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) 20731 diethyl 2-phenethylmalonate C15H20O4 详情 详情
(XV) 20732 2-(ethoxycarbonyl)-4-phenylbutyric acid C13H16O4 详情 详情
(XVI) 20733 ethyl 2-phenethylacrylate C13H16O2 详情 详情
(XVII) 20734 cyclopentanecarboxylic acid 3400-45-1 C6H10O2 详情 详情
Extended Information