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【结 构 式】 
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【分子编号】52319 【品名】3-(1,1-dimethylethyl) 5-methyl 2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3,5-dicarboxylate 【CA登记号】 |
【 分 子 式 】C19H27NO5 【 分 子 量 】349.42712 【元素组成】C 65.31% H 7.79% N 4.01% O 22.89% |
合成路线1
该中间体在本合成路线中的序号：(III)Hydroxy amino ester (I) was protected as the oxazolidine (III) upon heating with 2,2-dimethoxypropane (II) in the presence of p-toluenesulfonic acid. Conversion of the ester group of (III) into aldehyde (V) was accomplished by reduction to alcohol (IV) with LiAlH4, followed by NaOCl oxidation catalyzed by 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) and NaBr. Addition of 3-(benzyloxy)propylmagnesium bromide (VI) to aldehyde (V) furnished carbinol (VII), which was further protected as the silyl ether (VIII) by treatment with tert-butyldimethylsilyl chloride and imidazole. After hydrogenolysis of the O-benzyl protecting group of (VIII), the resultant primary alcohol (IX) was converted to bromide (X) employing the N-bromosuccinimide/triphenylphosphine reagent.
| 【1】 Doggrell, S.A.; Castaner, J.; NK-3201. Drugs Fut 2003, 28, 4, 323. |
| 【2】 Suzuki, Y.; Ishida, K. (Nippon Kayaku Co., Ltd.); Novel acetamide derivs. and protease inhibitors. EP 0936216; US 6271238; WO 9809949 . |
| 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) | 52327 | methyl 3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-4-phenylbutanoate | C16H23NO5 | 详情 | 详情 | |
| (II) | 10722 | 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane | 77-76-9 | C5H12O2 | 详情 | 详情 |
| (III) | 52319 | 3-(1,1-dimethylethyl) 5-methyl 2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3,5-dicarboxylate | C19H27NO5 | 详情 | 详情 | |
| (IV) | 52320 | 1,1-dimethylethyl 5-(hydroxymethyl)-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C18H27NO4 | 详情 | 详情 | |
| (V) | 52321 | 1,1-dimethylethyl 5-formyl-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C18H25NO4 | 详情 | 详情 | |
| (VI) | 52322 | bromo{3-[(phenylmethyl)oxy]propyl}magnesium | C10H13BrMgO | 详情 | 详情 | |
| (VII) | 52323 | 1,1-dimethylethyl 5-{1-hydroxy-4-[(phenylmethyl)oxy]butyl}-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C28H39NO5 | 详情 | 详情 | |
| (VIII) | 52324 | 1,1-dimethylethyl 5-{1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-[(phenylmethyl)oxy]butyl}-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C34H53NO5Si | 详情 | 详情 | |
| (IX) | 52325 | 1,1-dimethylethyl 5-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-hydroxybutyl)-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C27H47NO5Si | 详情 | 详情 | |
| (X) | 52326 | 1,1-dimethylethyl 5-(4-bromo-1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}butyl)-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate | C27H46BrNO4Si | 详情 | 详情 |