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【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%

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:(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
Extended Information