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【结 构 式】

【分子编号】26554

【品名】tert-butyl 4-[[(4-[[(hexylamino)carbonyl]amino]phenyl)sulfonyl]amino]phenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate

【CA登记号】

【 分 子 式 】C33H45N5O6S

【 分 子 量 】639.8164

【元素组成】C 61.95% H 7.09% N 10.95% O 15% S 5.01%

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:(XII)

Chlorination of 3-acetylpyridine (V) with N-chlorosuccinimide in HCl-AcOH gave (chloroacetyl)pyridine (VI). Subsequent enantioselective reduction of (VI) using (-)-B-chlorodiisopinocampheylborane yielded (R)-chlorohydrin (VII), which was cyclized to pyridyloxirane (VIII) with K2CO3 in boiling acetone. Opening of epoxide (VIII) with 4-aminophenethylamine (IX) produced amino alcohol (X). After protection as the tert-butyl carbamate (XI), coupling with sulfonyl chloride (IV) furnished sulfonamide (XII). Finally, Boc deprotection of (XII) using TFA produced the title compound.

1 Fisher, M.H.; Naylor, E.M.; Ok, D.; Weber, A.E.; Shih, T.; Ok, H. (Merck & Co., Inc.); Substd. sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. EP 0757674; JP 1997512275; US 5541197; US 5561142; WO 9529159 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 26548 4-[[(hexylamino)carbonyl]amino]benzenesulfonyl chloride C13H19ClN2O3S 详情 详情
(V) 12027 1-(3-Pyridinyl)-1-ethanone; 1-(3-Pyridinyl)ethanone 350-03-8 C7H7NO 详情 详情
(VI) 26549 2-chloro-1-(3-pyridinyl)-1-ethanone C7H6ClNO 详情 详情
(VII) 26550 (1R)-2-chloro-1-(3-pyridinyl)-1-ethanol C7H8ClNO 详情 详情
(VIII) 26551 3-[(2R)oxiranyl]pyridine C7H7NO 详情 详情
(IX) 18961 4-(2-aminoethyl)aniline; 4-(2-aminoethyl)phenylamine 13472-00-9 C8H12N2 详情 详情
(X) 26552 (1R)-2-[(4-aminophenethyl)amino]-1-(3-pyridinyl)-1-ethanol C15H19N3O 详情 详情
(XI) 26553 tert-butyl 4-aminophenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate C20H27N3O3 详情 详情
(XII) 26554 tert-butyl 4-[[(4-[[(hexylamino)carbonyl]amino]phenyl)sulfonyl]amino]phenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate C33H45N5O6S 详情 详情
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