ethyl 2-[5-[(E)-3-(diethylamino)-1-methyl-3-oxo-1-propenyl]-2-[(2,6-difluorobenzyl)oxy]phenoxy]acetate -Drug Synthesis Database

【结构式】

【分子编号】22321

【品名】ethyl 2-[5-[(E)-3-(diethylamino)-1-methyl-3-oxo-1-propenyl]-2-[(2,6-difluorobenzyl)oxy]phenoxy]acetate

【CA登记号】

【分子式】C₂₅H₂₉F₂NO₅

【分子量】461.5058064

【元素组成】C 65.06% H 6.33% F 8.23% N 3.04% O 17.33%

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：(VII)

3',4'-Dihydroxyacetophenone (I) was selectively alkylated at position 4' with alpha-bromo-2,6-difluorotoluene (II) in the presence of Li2CO3 in DMF. The resulting ether (III) was further alkylated with ethyl bromoacetate (IV) to give (V). Subsequent Horner-Emmons condensation of (V) with the phosphonoacetamide (VI) provided cinnamide (VII). The target carboxylic acid was then obtained by saponification of the ethyl ester of (VII) with NaOH.

参考文献中间体

合成目标

【1】 Greenspan, P.D.; Fujimoto, R.A.; Marshall, P.J.; Raychaudhuri, A.; Lipson, K.E.; Zhou, H.; Doti, R.A.; Coppa, D.E.; Zhu, L.; Pelletier, R.; Uziel-Fusi, S.; Jackson, R.H.; Chin, M.H.; Kotyuk, B.L.; Fitt, J.J.; Carboxy-substituted cinnamides: A novel series of potent, orally active LTB4 receptor antagonists. J Med Chem 1999, 42, 1, 164.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	22315	1-(3,4-dihydroxyphenyl)-1-ethanone	1197-09-7	C₈H₈O₃	详情	详情
(II)	22316	2-(bromomethyl)-1,3-difluorobenzene	85118-00-9	C₇H₅BrF₂	详情	详情
(III)	22317	1-[4-[(2,6-difluorobenzyl)oxy]-3-hydroxyphenyl]-1-ethanone		C₁₅H₁₂F₂O₃	详情	详情
(IV)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(V)	22319	ethyl 2-[5-acetyl-2-[(2,6-difluorobenzyl)oxy]phenoxy]acetate		C₁₉H₁₈F₂O₅	详情	详情
(VI)	22320	diethyl 2-(diethylamino)-2-oxoethylphosphonate		C₁₀H₂₂NO₄P	详情	详情
(VII)	22321	ethyl 2-[5-[(E)-3-(diethylamino)-1-methyl-3-oxo-1-propenyl]-2-[(2,6-difluorobenzyl)oxy]phenoxy]acetate		C₂₅H₂₉F₂NO₅	详情	详情

Extended Information