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【结 构 式】

【分子编号】52476

【品名】O-methyl-4-oxo-N-{[(phenylmethyl)oxy]carbonyl}homoserine

【CA登记号】

【 分 子 式 】C13H15NO6

【 分 子 量 】281.26524

【元素组成】C 55.51% H 5.38% N 4.98% O 34.13%

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)

Condensation of tert-butyl 4-fluoro-3-(bromomethyl)benzoate (I) with N-Boc-1,3-propanediamine (II) afforded the aminomethyl benzoate derivative (III). This was coupled with N-Cbz-L-aspartic acid beta-methyl ester (IV), yielding amide (V). After hydrogenolysis of the carbobenzoxy protecting group of (V), the resultant fluoro amine (VI) was cyclized to the benzodiazepinone (VII) upon treatment with 2,6-di-tert-butylpyridine in hot NMP. Acidic cleavage of both the tert-butyl ester and the N-Boc groups of (VII), followed by reprotection of the amine with Boc2O, furnished the N-Boc acid (VIII). This was then coupled to 2-(methylaminomethyl)benzimidazole (IX) to afford, after acidic Boc group cleavage, the amino amide (X).

1 Cheesman, E.H.; et al.; Nonpeptide vitronectin antagonists labeled with Tc99m for imaging tumors. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 77.
2 Sworin, M.; Cheesman, E.H.; Rajopadhyem, M. (DuPont Pharmaceuticals Co.); Vitronectin receptor antagonist pharmaceuticals. EP 1140864; WO 0035887 .
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) 52473 1,1-dimethylethyl 3-(bromomethyl)-4-fluorobenzoate C12H14BrFO2 详情 详情
(II) 52474 1,1-dimethylethyl 3-aminopropylcarbamate C8H18N2O2 详情 详情
(III) 52475 1,1-dimethylethyl 3-({[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]amino}methyl)-4-fluorobenzoate C20H31FN2O4 详情 详情
(IV) 52476 O-methyl-4-oxo-N-{[(phenylmethyl)oxy]carbonyl}homoserine C13H15NO6 详情 详情
(V) 52477 1,1-dimethylethyl 3-({[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl][4-(methyloxy)-4-oxo-2-({[(phenylmethyl)oxy]carbonyl}amino)butanoyl]amino}methyl)-4-fluorobenzoate C33H44FN3O9 详情 详情
(VI) 52478 1,1-dimethylethyl 3-({[2-amino-4-(methyloxy)-4-oxobutanoyl][3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]amino}methyl)-4-fluorobenzoate C25H38FN3O7 详情 详情
(VII) 52479 1,1-dimethylethyl 4-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]-2-[2-(methyloxy)-2-oxoethyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate C25H37N3O7 详情 详情
(VIII) 52480 4-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]-2-[2-(methyloxy)-2-oxoethyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid C21H29N3O7 详情 详情
(IX) 52481 1H-benzimidazol-2-yl-N-methylmethanamine; N-(1H-benzimidazol-2-ylmethyl)-N-methylamine C9H11N3 详情 详情
(X) 52482 methyl 2-(4-(3-aminopropyl)-7-{[(1H-benzimidazol-2-ylmethyl)(methyl)amino]carbonyl}-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-yl)acetate C25H30N6O4 详情 详情
Extended Information