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【结 构 式】

【分子编号】34531

【品名】4-ethoxy-2-[2-(3-methoxybenzyl)phenyl]-4-oxobutyric acid

【CA登记号】

【 分 子 式 】C20H22O5

【 分 子 量 】342.39168

【元素组成】C 70.16% H 6.48% O 23.36%

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:(XIX)

The synthesis of the tricyclic precursors has been reported by two alternative routes. Alkylation of 3-(3-methoxyphenyl)indene (XVI) with ethyl bromoacetate using lithium hexamethyldisilazide provided indeneacetate (XVII). Subsequent oxidative cleavage of (XVII) gave rise to the arylsuccinic derivative (XVIII). The benzoyl group of (XVIII) was then reduced to the benzyl analogue (XIX) by catalytic hydrogenation in the presence of Pd/C in AcOH. After conversion of (XIX) to the corresponding acid chloride (XX), Friedel-Crafts cyclization produced the tricyclic ketoester (XXI). Then reduction of the ketone group of (XXI) by hydrogenation over Pd/C furnished intermediate (IX).

1 Miller, W.H.; Samanen, J.M.; Heerding, D.; Bondinell, W.E. (SmithKline Beecham Corp.); Vitronectin receptor antagonists. EP 1025090; WO 9915508 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(IX) 34522 ethyl 2-(3-methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)acetate C20H22O3 详情 详情
(XVI) 34528 3-(3-methoxyphenyl)-1H-indene; 3-(1H-inden-3-yl)phenyl methyl ether C16H14O 详情 详情
(XVII) 34529 ethyl 2-[3-(3-methoxyphenyl)-1H-inden-1-yl]acetate C20H20O3 详情 详情
(XVIII) 34530 4-ethoxy-2-[2-(3-methoxybenzoyl)phenyl]-4-oxobutyric acid C20H20O6 详情 详情
(XIX) 34531 4-ethoxy-2-[2-(3-methoxybenzyl)phenyl]-4-oxobutyric acid C20H22O5 详情 详情
(XX) 34532 ethyl 4-chloro-3-[2-(3-methoxybenzyl)phenyl]-4-oxobutanoate C20H21ClO4 详情 详情
(XXI) 34533 ethyl 2-(3-methoxy-11-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)acetate C20H20O4 详情 详情
Extended Information