• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】60867

【品名】diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

【CA登记号】

【 分 子 式 】C16H16O6

【 分 子 量 】304.29944

【元素组成】C 63.15% H 5.3% O 31.55%

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:(III)

Claisen condensation between diethyl phthalate (I) and diethyl succinate (II) in the presence of NaOEt gives rise to the naphthalenedicarboxylate (III). Alkylation of the phenolic hydroxyl groups of (III) with iodoethane under Williamsom's ether synthesis conditions furnishes the diethoxy napthalenedicarboxylate (IV). Then, alkaline hydrolysis of diester (IV) affords diacid (V), which is further converted to the cyclic anhydride (VI) upon treatment with SOCl2. Condensation of anhydride (VI) with ethyl p-aminophenylacetate (VII) in boiling AcOH leads to the cyclic imide (VIII). Partial reduction of (VIII) with Zn/AcOH produces lactam (IX). The ethyl ester group of (IX) is then selectively hydrolyzed under alkaline conditions to furnish acid (X). Finally, CDI-mediated coupling of acid (X) with benzesulfonamide yields the target N-acyl sulfonamide.

1 Giblin, G.M.P.; Foord, S.; Wilson, R.; et al.; Novel nonprostanoid prostaglandin EP4 receptor antagonist. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 306.
2 Frye, S.V.; Giblin, G.M.P.; Roomans, S. (GlaxoSmithKline plc); Benzo(f)isoindol derivs. and their use as EP4 receptor ligands. WO 0250033 .
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) 60866 diethyl phthalate C12H14O4 详情 详情
(II) 12313 diethyl succinate 123-25-1 C8H14O4 详情 详情
(III) 60867 diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate C16H16O6 详情 详情
(IV) 60868 diethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate C20H24O6 详情 详情
(V) 60869 1,4-diethoxy-2,3-naphthalenedicarboxylic acid C16H16O6 详情 详情
(VI) 60870 4,9-diethoxynaphtho[2,3-c]furan-1,3-dione C16H14O5 详情 详情
(VII) 21230 ethyl 2-(4-aminophenyl)acetate 5438-70-0 C10H13NO2 详情 详情
(VIII) 60871 ethyl 2-[4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate C26H25NO6 详情 详情
(IX) 60872 ethyl 2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate C26H27NO5 详情 详情
(X) 60873 2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid C24H23NO5 详情 详情
Extended Information