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【结 构 式】

【分子编号】62380

【品名】(3S)-4-(benzoylamino)-3-(3,4-dichlorophenyl)butyl methanesulfonate

【CA登记号】

【 分 子 式 】C18H19Cl2NO4S

【 分 子 量 】416.3246

【元素组成】C 51.93% H 4.6% Cl 17.03% N 3.36% O 15.37% S 7.7%

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:(XIII)

Alkylation of 3,4-dichlorophenylacetonitrile (VI) with (tetrahydropyranyloxy)ethyl bromide (V) (prepared by protection of 2-bromoethanol (IV) with dihydropyran) furnished nitrile (VII). Catalytic hydrogenation of (VII) in the presence of Raney-Ni and Et3N gave the primary amine (VIII). After acidic hydrolysis of the tetrahydropyranyl group of (VIII), the resultant amino alcohol was resolved by means of D-tartaric acid providing the (S)-enantiomer (IX). Reaction of amine (IX) with ethyl chloroformate afforded carbamate (X), which was further reduced to the N-methyl amine (XI) employing LiAlH4. Subsequent acylation of (XI) with benzoyl chloride furnished benzamide (XII). Mesylate (XIII) was then prepared by treatment of alcohol (XII) with methanesulfonyl chloride and triethylamine. Finally, condensation between piperidine (III) and mesylate (XIII) led to the title compound

1 Emonds-Alt, X.; Goulaouic, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthelabo); Arylalkylamines, process for their preparation and pharmaceutical compsns. containing them. EP 0474561; FR 2666335; FR 2678267; JP 1992261155; US 5236921; US 5350852 .
2 Emonds-Alt, X.; Proietto, V.; Van Broeck, D.; Vilain, P.; Advenier, C.; Neliat, G.; Le Fur, G.; Breliere, J.-C.; Pharmacological profile and chemical synthesis of SR 48968, a non-peptide antagonist of the neurokinin A (NK2) receptor. Bioorg Med Chem Lett 1993, 3, 5, 925.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 59283 N-(4-phenyl-4-piperidinyl)acetamide C13H18N2O 详情 详情
(IV) 10059 Ethylene bromohydrin; 2-Bromo-1-ethanol 540-51-2 C2H5BrO 详情 详情
(V) 26934 2-bromoethyl tetrahydro-2H-pyran-2-yl ether C7H13BrO2 详情 详情
(VI) 26935 2-(3,4-dichlorophenyl)acetonitrile 3218-49-3 C8H5Cl2N 详情 详情
(VII) 26936 2-(3,4-dichlorophenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butanenitrile C15H17Cl2NO2 详情 详情
(VIII) 26937 2-(3,4-dichlorophenyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanamine C15H21Cl2NO2 详情 详情
(IX) 26939 (3S)-4-amino-3-(3,4-dichlorophenyl)-1-butanol C10H13Cl2NO 详情 详情
(X) 26940 ethyl (2S)-2-(3,4-dichlorophenyl)-4-hydroxybutylcarbamate C13H17Cl2NO3 详情 详情
(XI) 26941 (3S)-3-(3,4-dichlorophenyl)-4-(methylamino)-1-butanol C11H15Cl2NO 详情 详情
(XII) 26942 N-[(2S)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methylbenzamide C18H19Cl2NO2 详情 详情
(XIII) 62380 (3S)-4-(benzoylamino)-3-(3,4-dichlorophenyl)butyl methanesulfonate C18H19Cl2NO4S 详情 详情
Extended Information