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【结 构 式】

【分子编号】52325

【品名】1,1-dimethylethyl 5-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-hydroxybutyl)-2,2-dimethyl-4-(phenylmethyl)-1,3-oxazolidine-3-carboxylate

【CA登记号】

【 分 子 式 】C27H47NO5Si

【 分 子 量 】493.75942

【元素组成】C 65.68% H 9.59% N 2.84% O 16.2% Si 5.69%

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)

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
Extended Information