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【结 构 式】

【分子编号】38031

【品名】tert-butyl 4-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]benzoate

【CA登记号】

【 分 子 式 】C23H25NO4

【 分 子 量 】379.45584

【元素组成】C 72.8% H 6.64% N 3.69% O 16.87%

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:(IV)

The condensation of tert-butyl 4-iodobenzoate (I) with N-(3-butenyl)phthalimide (II) by means of palladium acetate and tri-p-tolylphosphine in TEA at 110 C gives 4-(4-phthalimido-1-butenyl)benzoic acid tert-butyl ester (III), which is hydrogenated with H2 over Pd/C in THF/ethanol yielding the corresponding butyl derivative (IV). The treatment of (IV) with hydrazine in refluxing ethanol affords 4-(4-aminobutyl)benzoic acid tert-butyl ester (V), which is cyclized with 2-sulfanylsuccinic acid (VI) and octanal (VII) in refluxing toluene to provide the thiazolidinone (VIII). The condensation of (VIII) with dibenzylamine (IX) by means of HOBT and EDC in dichloromethane, followed by chromatographic separation of the undesired (2R*,5S*)-isomer, yields the (2S*,5S*)-dibenzylamide (X). Finally, this compound is hydrolyzed with TFA in dichloromethane affording the target benzoic acid.

1 Willson, T.M.; Holmes, C.P.; Collins, J.L.; Lenhard, J.M. (Glaxo Group Ltd.); PPARgamma ligands. WO 0027832 .
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) 38028 tert-butyl 4-iodobenzoate C11H13IO2 详情 详情
(II) 38029 2-(3-butenyl)-1H-isoindole-1,3(2H)-dione 52898-32-5 C12H11NO2 详情 详情
(III) 38030 tert-butyl 4-[(E)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-butenyl]benzoate C23H23NO4 详情 详情
(IV) 38031 tert-butyl 4-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]benzoate C23H25NO4 详情 详情
(V) 38032 tert-butyl 4-(4-aminobutyl)benzoate C15H23NO2 详情 详情
(VI) 38033 2-sulfanylsuccinic acid 70-49-5 C4H6O4S 详情 详情
(VII) 25714 octanal 124-13-0 C8H16O 详情 详情
(VIII) 38034 2-((2S,5R)-3-[4-[4-(tert-butoxycarbonyl)phenyl]butyl]-2-heptyl-4-oxo-1,3-thiazolidin-5-yl)acetic acid C27H41NO5S 详情 详情
(IX) 12361 N,N-Dibenzylamine; Dibenzylamine; N-Benzyl(phenyl)methanamine 103-49-1 C14H15N 详情 详情
(X) 38035 tert-butyl 4-(4-[(2S,5R)-5-[2-(dibenzylamino)-2-oxoethyl]-2-heptyl-4-oxo-1,3-thiazolidin-3-yl]butyl)benzoate C41H54N2O4S 详情 详情
Extended Information