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【结 构 式】 
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【分子编号】30450 【品名】4-[3-(3-cyclopentylpropyl)-2-oxo-1-imidazolidinyl]benzenesulfonyl chloride 【CA登记号】 |
【 分 子 式 】C17H23ClN2O3S 【 分 子 量 】370.9 【元素组成】C 55.05% H 6.25% Cl 9.56% N 7.55% O 12.94% S 8.65% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The chlorination of 3-acetylpyridine (I) with N-chlorosuccinimide (NCS) in acetic acid gives 3-(2-chloroacetyl)pyridine (II), which is reduced with (-)-B-chlorodiisopinocampheylborane [(-)-DIP-Cl] yielding the chiral chloroethanol (III). The epoxidation of (III) with K2CO3 in refluxing acetone affords the chiral epoxide (IV), which is opened with 4-(2-aminoethyl)aniline (V) in refluxing methanol giving the chiral aminoethanol (VI). The protection of the aliphatic amino group of (VI) with di-tert-butyl dicarbonate yields the carbamate (VII), which is finally condensed with the sulfonyl chloride (VIII) by means of pyridine in dichloromethane and deprotected with TFA in the same solvent.
| 【1】 Colandrea, V.J.; Naylor, E.M.; Parmee, E.R.; et al.; Human beta3 adrenergic receptor agonists containing imidazolidinone and imidazolone benzenesulfonamides. Bioorg Med Chem Lett 1999, 9, 5, 755. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (I) | 10027 | Benzyl (1S)-1-[[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl]-3-butenyl(benzyl)carbamate | C28H35NO6 | 详情 | 详情 | |
| (II) | 26549 | 2-chloro-1-(3-pyridinyl)-1-ethanone | C7H6ClNO | 详情 | 详情 | |
| (III) | 26550 | (1R)-2-chloro-1-(3-pyridinyl)-1-ethanol | C7H8ClNO | 详情 | 详情 | |
| (IV) | 26551 | 3-[(2R)oxiranyl]pyridine | C7H7NO | 详情 | 详情 | |
| (V) | 18961 | 4-(2-aminoethyl)aniline; 4-(2-aminoethyl)phenylamine | 13472-00-9 | C8H12N2 | 详情 | 详情 |
| (VI) | 26552 | (1R)-2-[(4-aminophenethyl)amino]-1-(3-pyridinyl)-1-ethanol | C15H19N3O | 详情 | 详情 | |
| (VII) | 30449 | (1R)-2-[(4-aminophenethyl)[1-(tert-butoxy)vinyl]amino]-1-(3-pyridinyl)-1-ethanol | C21H29N3O2 | 详情 | 详情 | |
| (VIII) | 30450 | 4-[3-(3-cyclopentylpropyl)-2-oxo-1-imidazolidinyl]benzenesulfonyl chloride | C17H23ClN2O3S | 详情 | 详情 |