methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】57378

【品名】methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoate

【CA登记号】

【分子式】C₂₄H₂₆N₂O₃

【分子量】390.48212

【元素组成】C 73.82% H 6.71% N 7.17% O 12.29%

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：(VIII)

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).

参考文献中间体

合成目标

【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