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【结 构 式】

【分子编号】27812

【品名】tert-butyl (2S)-2-hydroxy-3-(3-pyridinyloxy)propyl(4-[[(4-iodophenyl)sulfonyl]amino]phenethyl)carbamate

【CA登记号】

【 分 子 式 】C27H32IN3O6S

【 分 子 量 】653.53817

【元素组成】C 49.62% H 4.94% I 19.42% N 6.43% O 14.69% S 4.91%

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:(IX)

The reaction of 3-hydroxypyridine (I) with (S)-glycidol 3-nitrobenzenesulfonate (II) by means of sodium hexamethyldisylazide in DMSO gives 2(S)-(3-pyridyloxymethyl)oxirane (III), which is condensed with 2-(4-nitrophenyl)ethylamine (IV) by means of triethylamine in refluxing methanol yielding the chiral isopropanol (V). The protection of the secondary amino group of (V) with tert-butoxycarbonyl anhydride affords the carbamate (VI), which is submitted to reduction at the nitro group with H2 over palladium hydroxide in ethyl acetate providing the aniline derivative (VII). The acylation of (VII) with 4-iodobenzenesulfonyl chloride (VIII) and pyridine in dichloromethane affords the sulfonamide (IX), which is finally deprotected with 6N HCl in methanol.

1 Fisher, M.H.; Mathvink, R.J.; Ok, H.O.; Parmee, E.R.; Weber, A.E. (Merck & Co., Inc.); Substd. phenyl sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. CA 2114712; EP 0611003; JP 1995010827; US 5451677; WO 9418161 .
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) 12911 3-Hydroxypyridine; 3-Pyridinol 109-00-2 C5H5NO 详情 详情
(II) 16259 (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate 115314-14-2 C9H9NO6S 详情 详情
(III) 27807 (2S)oxiranylmethyl 3-pyridinyl ether C8H9NO2 详情 详情
(IV) 26560 4-nitrophenethylamine 24954-67-4 C8H10N2O2 详情 详情
(V) 27808 (2S)-1-[(4-nitrophenethyl)amino]-3-(3-pyridinyloxy)-2-propanol C16H19N3O4 详情 详情
(VI) 27809 tert-butyl (2S)-2-hydroxy-3-(3-pyridinyloxy)propyl(4-nitrophenethyl)carbamate C21H27N3O6 详情 详情
(VII) 27810 tert-butyl 4-aminophenethyl[(2S)-2-hydroxy-3-(3-pyridinyloxy)propyl]carbamate C21H29N3O4 详情 详情
(VIII) 27811 4-iodobenzenesulfonyl chloride 98-61-3 C6H4ClIO2S 详情 详情
(IX) 27812 tert-butyl (2S)-2-hydroxy-3-(3-pyridinyloxy)propyl(4-[[(4-iodophenyl)sulfonyl]amino]phenethyl)carbamate C27H32IN3O6S 详情 详情
Extended Information