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【结 构 式】

【分子编号】18083

【品名】2-[3-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetic acid

【CA登记号】

【 分 子 式 】C27H28N4O6

【 分 子 量 】504.54268

【元素组成】C 64.28% H 5.59% N 11.1% O 19.03%

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:(XII)

Alkylation of 3-nitrophenol (I) with methyl bromoacetate (II) in the presence of K2CO3 provided phenoxyacetate (III). Then, reduction of the nitro group of (III) by hydrogenation on Pd/C gave amine (IV), which was subsequently condensed with N-tert-butoxycarbonyl glycine (V) on treatment with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) to afford amide (VI). Alkylation with bromoacetamide (VII) in the presence of NaH in THF provided (VIII), and removal of the Boc protecting group with trifluoroacetic acid gave amine (IX). This amine was condensed with 3-tolyl isocyanate (X) to give urea (XI). Then, alkaline hydrolysis of the ester group afforded acid (XII), which was finally condensed with N-methylaniline (XIII) to yield the target compound.

1 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 .
2 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 .
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) 18076 Metanitrophenol; 3-nitrophenol 554-84-7 C6H5NO3 详情 详情
(II) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(III) 18077 methyl 2-(3-nitrophenoxy)acetate C9H9NO5 详情 详情
(IV) 18078 methyl 2-(3-aminophenoxy)acetate C9H11NO3 详情 详情
(V) 18066 N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid 4530-20-5 C7H13NO4 详情 详情
(V) 18068 2-bromo-N-methyl-N-phenylacetamide C9H10BrNO 详情 详情
(VI) 18079 methyl 2-[3-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)phenoxy]acetate C16H22N2O6 详情 详情
(VIII) 18080 methyl 2-(3-[[2-[(tert-butoxycarbonyl)amino]acetyl][2-(methylanilino)-2-oxoethyl]amino]phenoxy)acetate C25H31N3O7 详情 详情
(IX) 18081 methyl 2-(3-[(2-aminoacetyl)[2-(methylanilino)-2-oxoethyl]amino]phenoxy)acetate C20H23N3O5 详情 详情
(X) 18071 m-Tolyl Isocyanate; 1-isocyanato-3-methylbenzene; 3-methylphenyl isocyanate 621-29-4 C8H7NO 详情 详情
(XI) 18082 methyl 2-[3-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetate C28H30N4O6 详情 详情
(XII) 18083 2-[3-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetic acid C27H28N4O6 详情 详情
(XIII) 10409 N-Methyl-N-phenylamine; N-methylaniline; Monomethylaniline 100-61-8 C7H9N 详情 详情
Extended Information