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【结 构 式】

【分子编号】61614

【品名】methyl (2S,4E)-5-chloro-2-isopropyl-4-pentenoate

【CA登记号】

【 分 子 式 】C9H15ClO2

【 分 子 量 】190.6696

【元素组成】C 56.69% H 7.93% Cl 18.59% O 16.78%

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:(II)

The condensation of the chiral chloro derivative (I) with 5-chloro-[2(S)-isopropyl]-4-pentanoic acid methyl ester (II) by means of Mg and dibromoethane in THF gives the chiral octenoic ester (III) which is converted to the corresponding acid (IV) by means of LiOH in THF/methanol/water. The reaction of (IV) with NBS in dichloromethane yields the bromolactone (V), which is treated with LiOH in isopropanol to yield the epoxide (VI). This compound, without isolation, is treated with HCl in the same solvent to afford the chiral hydroxylactone (VII). The reaction of the OH group of (VII) with MsCl and pyridine in toluene provides the mesylate (VIII), which is treated with NaN3 in hot 1,3-dimethylperhydropyrimidin-2-one to give the azido derivative (IX). The condensation of (IX) with 3-amino-2,2-dimethylpropionamide (X) by means of 2-hydroxypyridine in hot TEA yields the carboxamide (XI). Finally, the azido group of (XI) is reduced with H2 over Pd/C in tert-butyl methyl ether to provide the target Aliskiren.

1 Herold, P.; Stutz, S.; Spindler, F. (Speedel Pharma Inc.); Process for the preparation of substd. octanoyl amides. WO 0202508 .
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) 50574 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene; 3-[5-[(2R)-2-(chloromethyl)-3-methylbutyl]-2-methoxyphenoxy]propyl methyl ether 324763-39-5 C17H27ClO3 详情 详情
(II) 61614 methyl (2S,4E)-5-chloro-2-isopropyl-4-pentenoate C9H15ClO2 详情 详情
(III) 61615 methyl (2S,4E,7R)-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-4-nonenoate C26H42O5 详情 详情
(IV) 61616 (2S,4E,7R)-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-4-nonenoic acid C25H40O5 详情 详情
(V) 61617 (3S,5R)-5-{(1S,3S)-1-bromo-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}-3-isopropyldihydro-2(3H)-furanone C25H39BrO5 详情 详情
(VI) 61618 lithium (2S)-2-[((2R,3R)-3-{(2S)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}oxiranyl)methyl]-3-methylbutanoate C25H39LiO6 详情 详情
(VII) 50576 (3S,5S)-5-[(1R,3S)-1-hydroxy-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl]-3-isopropyldihydro-2(3H)-furanone C25H40O6 详情 详情
(VIII) 61619 (1R,3S)-1-[(2S,4S)-4-isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate C26H42O8S 详情 详情
(IX) 50578 (3S,5S)-5-[(1S,3S)-1-azido-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl]-3-isopropyldihydro-2(3H)-furanone C25H39N3O5 详情 详情
(X) 28129 3-amino-2,2-dimethylpropanamide 324763-51-1 C5H12N2O 详情 详情
(XI) 61613 (2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide C30H51N5O6 详情 详情
Extended Information