【结 构 式】 |
【分子编号】34954 【品名】tert-butyl 2-[(4-[2-[[(2,4-difluoroanilino)carbonyl](heptyl)amino]ethyl]phenyl)sulfanyl]-2-methylpropanoate 【CA登记号】 |
【 分 子 式 】C30H42F2N2O3S 【 分 子 量 】548.7379664 【元素组成】C 65.67% H 7.71% F 6.92% N 5.11% O 8.75% S 5.84% |
合成路线1
该中间体在本合成路线中的序号:(XI)4-Bromothiophenol (I) was alkylated with tert-butyl bromoisobutyrate (II) to give the bromoester (III). Heck reaction of (III) with vinylphthalimide (IV) produced adduct (V), which was hydrogenated in the presence of Wilkinson's catalyst to yield the arylethyl phthalimide (VI). Following phthalimide deprotection with hydrazine, the resulting primary amine (VII) was coupled with heptanoic acid using diisopropyl carbodiimide and hydroxybenzotriazole affording amide (VIII). Borane reduction of (VIII) furnished the secondary amine (IX), which was condensed with 2,4-difluorophenyl isocyanate (X) to give urea (XI). Finally, trifluoroacetic acid-promoted cleavage of the tert-butyl ester of (IX) provided the title carboxylic acid.
【1】 Brown, P.J.; Winegar, D.A.; Plunket, K.D.; et al.; A ureido thiosobutyric acid (GW9578) is a subtype selective PPARalpha agonist with potent lipid lowering activity. J Med Chem 1999, 42, 19, 3785. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
35032 | heptanoic acid | 111-14-8 | C7H14O2 | 详情 | 详情 | |
(I) | 29626 | 4-bromophenylhydrosulfide; 4-bromobenzenethiol | 106-53-6 | C6H5BrS | 详情 | 详情 |
(II) | 34947 | tert-butyl 2-bromo-2-methylpropanoate | 23877-12-5 | C8H15BrO2 | 详情 | 详情 |
(III) | 34948 | tert-butyl 2-[(4-bromophenyl)sulfanyl]-2-methylpropanoate | C14H19BrO2S | 详情 | 详情 | |
(IV) | 32749 | 2-vinyl-1H-isoindole-1,3(2H)-dione | 3485-84-5 | C10H7NO2 | 详情 | 详情 |
(V) | 34949 | tert-butyl 2-([4-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]phenyl]sulfanyl)-2-methylpropanoate | C24H25NO4S | 详情 | 详情 | |
(VI) | 34950 | tert-butyl 2-([4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]phenyl]sulfanyl)-2-methylpropanoate | C24H27NO4S | 详情 | 详情 | |
(VII) | 34951 | tert-butyl 2-[[4-(2-aminoethyl)phenyl]sulfanyl]-2-methylpropanoate | C16H25NO2S | 详情 | 详情 | |
(VIII) | 34952 | tert-butyl 2-([4-[2-(heptanoylamino)ethyl]phenyl]sulfanyl)-2-methylpropanoate | C23H37NO3S | 详情 | 详情 | |
(IX) | 34953 | tert-butyl 2-([4-[2-(heptylamino)ethyl]phenyl]sulfanyl)-2-methylpropanoate | C23H39NO2S | 详情 | 详情 | |
(X) | 23255 | 2,4-difluorophenyl isocyanate; 2,4-difluoro-1-isocyanatobenzene | 59025-55-7 | C7H3F2NO | 详情 | 详情 |
(XI) | 34954 | tert-butyl 2-[(4-[2-[[(2,4-difluoroanilino)carbonyl](heptyl)amino]ethyl]phenyl)sulfanyl]-2-methylpropanoate | C30H42F2N2O3S | 详情 | 详情 |