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【结 构 式】

【分子编号】57377

【品名】methyl (2R)-3-(4-aminophenyl)-2-[(3,5-dimethylbenzoyl)(methyl)amino]propanoate

【CA登记号】

【 分 子 式 】C20H24N2O3

【 分 子 量 】340.42224

【元素组成】C 70.57% H 7.11% N 8.23% O 14.1%

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)

Esterification of 4-nitro-D-phenylalanine (I) with HCl/MeOH provides the amino ester (II). This is subsequently acylated with 3,5-dimethylbenzoyl chloride (III), yielding amide (IV). Alkylation of amide (IV) by means of iodomethane and NaH affords the N-methyl amide (V). The nitro group of (V) is then reduced to amine (VI) by catalytic hydrogenation over Pd/C. Clauson-Kaas condensation of amine (VI) with 2,5-dimethoxytetrahydrofuran (VII) leads to the pyrrole derivative (VIII). The methyl ester function of (VIII) is then hydrolyzed with LiOH to provide the carboxylic acid (IX).

1 Ksander, G.M.; Kukkola, P.J.; Robinson, L.A. (Novartis AG); N-aroylamino acid amides as endothelin inhibitors. EP 0821670; JP 1999505522; WO 9633170 .
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) 57380 (2R)-2-amino-3-(4-nitrophenyl)propanoic acid C9H10N2O4 详情 详情
(II) 57381 methyl (2R)-2-amino-3-(4-nitrophenyl)propanoate C10H12N2O4 详情 详情
(III) 57374 3,5-dimethylbenzoyl chloride C9H9ClO 详情 详情
(IV) 57375 methyl (2R)-2-[(3,5-dimethylbenzoyl)amino]-3-(4-nitrophenyl)propanoate C19H20N2O5 详情 详情
(V) 57376 methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-(4-nitrophenyl)propanoate C20H22N2O5 详情 详情
(VI) 57377 methyl (2R)-3-(4-aminophenyl)-2-[(3,5-dimethylbenzoyl)(methyl)amino]propanoate C20H24N2O3 详情 详情
(VII) 12132 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether 696-59-3 C6H12O3 详情 详情
(VIII) 57378 methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoate C24H26N2O3 详情 详情
(IX) 57379 (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoic acid C23H24N2O3 详情 详情
Extended Information