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【结 构 式】

【药物名称】DA-3797

【化学名称】 

【CA登记号】

【 分 子 式 】C34H35N5O5

【 分 子 量 】593.68855

【开发单位】Daiichi Pharm

【药理作用】0

合成路线1

2-Benzyloxyaniline (I) was acylated with N-tert-butoxycarbonyl glycine (II) by means of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide.HCl (EDC) to give amide (III). Alkylation with bromoacetamide (IV) in the presence of NaH in THF provided (V), and then removal of the Boc protecting group with trifluoroacetic acid gave amine (VI). This amine was condensed with 3-tolyl isocyanate (VII) to give the phenylurea (VIII). Cleavage of the benzyl group by hydrogenolysis on Pd/C provided phenol (IX), which was alkylated with methyl bromoacetate in the presence of K2CO3 to give ether (X). Alkaline hydrolysis of the ester group gave acid (XI), which was finally condensed with N-methylaniline (XII) by means of EDC to yield the target compound.

1 Takeda, Y.; et al.; Synthesis of phenoxyacetic acid derivatives as highly potent antagonists of gastrin/cholecystokinin-B receptors. Chem Pharm Bull 1998, 46, 3, 434-444.
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) 18070 2-amino-N-[2-(benzyloxy)phenyl]-N-[2-(methylanilino)-2-oxoethyl]acetamide C24H25N3O3 详情 详情
(VII) 18071 m-Tolyl Isocyanate; 1-isocyanato-3-methylbenzene; 3-methylphenyl isocyanate 621-29-4 C8H7NO 详情 详情
(VIII) 18072 2-(2-(benzyloxy)[2-[(3-toluidinocarbonyl)amino]acetyl]anilino)-N-methyl-N-phenylacetamide C32H32N4O4 详情 详情
(IX) 18073 2-(2-hydroxy[2-[(3-toluidinocarbonyl)amino]acetyl]anilino)-N-methyl-N-phenylacetamide C25H26N4O4 详情 详情
(X) 18074 methyl 2-[2-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetate C28H30N4O6 详情 详情
(XI) 18075 2-[2-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetic acid C27H28N4O6 详情 详情
(XII) 10409 N-Methyl-N-phenylamine; N-methylaniline; Monomethylaniline 100-61-8 C7H9N 详情 详情
Extended Information