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【结 构 式】

【分子编号】41107

【品名】tert-butyl 2-[2-hydroxy[2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethylcarbamate

【CA登记号】

【 分 子 式 】C22H27N3O5

【 分 子 量 】413.4736

【元素组成】C 63.91% H 6.58% N 10.16% O 19.35%

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:(VI)

Coupling of 2-benzyloxyaniline (I) with N-Boc-glycine (II) by means of EDC aforded amide (III). Subsequent N-alkylation of (III) with N-methyl-N-phenyl-2-bromoacetamide (IV) in the presence of NaH provided diamide (V). Hydrogenolysis of the benzyl ether of (V) over Pd/C gave phenol derivative (VI) (1). Phenol (VI) was then alkylated with bromoamide (IV) to furnish ether (VII). After cleavage of the Boc group of (VII) with trifluoroacetic acid, the resulting amine (VIII) was reacted with carbonyldiimidazole to produce imidazolide (IX), which was subsequently coupled with aniline (X) yielding urea (XI). Finally, basic hydrolysis of the methyl ester group of (XI) gave the title carboxylic acid.

1 Yokomizo, A.; Takeda, Y.; Kawagoe, K.; et al.; Synthesis of phenoxyacetic acid derivatives as highly potent antagonists of gastrin/cholecystokinin-B receptors. II. Chem Pharm Bull 1998, 46, 6, 951.
2 Yokohama, S.; Kawagoe, K.; Takeda, Y.; Yokomizo, Y.; Yokomizo, A. (Daiichi Pharmaceutical Co., Ltd.); Aminophenol derivs.. EP 0985660; US 5919824; WO 9628416 .
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) 18065 2-(benzyloxy)aniline; 2-(benzyloxy)phenylamine C13H13NO 详情 详情
(II) 18066 N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid 4530-20-5 C7H13NO4 详情 详情
(III) 18067 tert-butyl 2-[2-(benzyloxy)anilino]-2-oxoethylcarbamate C20H24N2O4 详情 详情
(IV) 18068 2-bromo-N-methyl-N-phenylacetamide C9H10BrNO 详情 详情
(V) 18069 tert-butyl 2-[2-(benzyloxy)[2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethylcarbamate C29H33N3O5 详情 详情
(VI) 41107 tert-butyl 2-[2-hydroxy[2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethylcarbamate C22H27N3O5 详情 详情
(VII) 41108 tert-butyl 2-[2-[2-(methylanilino)-2-oxoethoxy][2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethylcarbamate C31H36N4O6 详情 详情
(VIII) 41109 2-amino-N-[2-[2-(methylanilino)-2-oxoethoxy]phenyl]-N-[2-(methylanilino)-2-oxoethyl]acetamide C26H28N4O4 详情 详情
(IX) 41110 N-(2-[2-[2-(methylanilino)-2-oxoethoxy][2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethyl)-1H-imidazole-1-carboxamide C30H30N6O5 详情 详情
(X) 41111 methyl 2-(3-aminophenyl)acetate C9H11NO2 详情 详情
(XI) 41112 methyl 2-[3-([[(2-[2-[2-(methylanilino)-2-oxoethoxy][2-(methylanilino)-2-oxoethyl]anilino]-2-oxoethyl)amino]carbonyl]amino)phenyl]acetate C36H37N5O7 详情 详情
Extended Information