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【结 构 式】

【分子编号】50348

【品名】2-methyl-5-phenyl-1,3-oxazole

【CA登记号】

【 分 子 式 】C10H9NO

【 分 子 量 】159.1876

【元素组成】C 75.45% H 5.7% N 8.8% O 10.05%

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:(III)

The cyclization of phenacyl bromide (I) with acetamide (II) by heating at 130 C gives 2-methyl-5-phenyloxazole (III), which is brominated with NBS in CCl4 to yield the dibromo derivative (IV). The condensation of (IV) with cyclopentylmethylmagnesium bromide (V) by means of Li2CuCl4 affords 4-bromo-2-(2-cyclopentylethyl)-5-phenyloxazole (VI), which is debrominated by hydrogenation with H2 over Pd(OH)2 in methanol, providing 2-(2-cyclopentylethyl)-5-phenyloxazole (VII). The sulfonation of the phenyl ring of (VII) with chlorosulfonic acid gives the sulfonyl chloride (VIII), which is condensed with the aniline derivative (IX) by means of pyridine in dichloromethane to yield the sulfonamide (X). Finally, elimination of the Boc protecting group of (X) by means of HCl in methanol affords the target compound.

1 Candelore, M.R.; Ok, H.O.; Reigle, L.B.; et al.; Substituted oxazole benzenesulfonamides as potent human beta3-adrenergic receptor agonist. Bioorg Med Chem Lett 2000, 10, 14, 1531.
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) 10315 2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone 70-11-1 C8H7BrO 详情 详情
(II) 50352 Acetamide; Acetic acid amide; Ethanamide 60-35-5 C2H5NO 详情 详情
(III) 50348 2-methyl-5-phenyl-1,3-oxazole C10H9NO 详情 详情
(IV) 50349 4-bromo-2-(bromomethyl)-5-phenyl-1,3-oxazole C10H7Br2NO 详情 详情
(V) 50350 bromo(cyclopentylmethyl)magnesium C6H11BrMg 详情 详情
(VI) 50351 4-bromo-2-(2-cyclopentylethyl)-5-phenyl-1,3-oxazole C16H18BrNO 详情 详情
(VII) 26723 2-(2-cyclopentylethyl)-5-phenyl-1,3-oxazole C16H19NO 详情 详情
(VIII) 26718 4-[2-(2-cyclopentylethyl)-1,3-oxazol-5-yl]benzenesulfonyl chloride C16H18ClNO3S 详情 详情
(IX) 26553 tert-butyl 4-aminophenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate C20H27N3O3 详情 详情
(X) 26718 4-[2-(2-cyclopentylethyl)-1,3-oxazol-5-yl]benzenesulfonyl chloride C16H18ClNO3S 详情 详情
Extended Information