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【结 构 式】

【分子编号】25935

【品名】4-(tert-butoxycarbonyl)-1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylic acid

【CA登记号】

【 分 子 式 】C17H24N2O7S

【 分 子 量 】400.45284

【元素组成】C 50.99% H 6.04% N 7% O 27.97% S 8.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The selective protection of piperazine-2-carboxylic acid (I) with tert-butoxycarbonyl anhydride gives the carbamate (II), which is sulfonated with 4-methoxybenzenesulfonyl chloride (II) and triethylamine yielding the sulfonamide (IV). The esterification and simultaneous deprotection of (IV) with SOCl2 and methanol affords the methyl ester (V), which is treated with benzyl chloroformate (VI) and triethylamine to afford the benzyloxycarbonyl derivative (VII). Finally, this compound is treated with KOH and hydroxylamine in methanol to provide the target hydroxamic acid.

1 Pikul, S.; Natchus, M.G.; Cheng, M.; et al.; Design and synthesis of piperazine-based MMP inhibitors. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 044.
2 De, B.; Natchus, M.G.; Pikul, S.; Almstead, N.G.; Matthews, R.S.; Taiwo, Y.O.; Cheng, M. (The Procter & Gamble Co.); 1,4-Heterocyclic metalloprotease inhibitors. EP 0923563; EP 0925287; WO 9808825; WO 9808827 .
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) 25933 2-piperazinecarboxylic acid; Piperazine-2-carboxylic acid C5H10N2O2 详情 详情
(II) 25934 4-(tert-butoxycarbonyl)-2-piperazinecarboxylic acid C10H18N2O4 详情 详情
(III) 15719 4-methoxybenzenesulfonyl chloride 98-68-0 C7H7ClO3S 详情 详情
(IV) 25935 4-(tert-butoxycarbonyl)-1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylic acid C17H24N2O7S 详情 详情
(V) 25936 methyl 1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylate C13H18N2O5S 详情 详情
(VI) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(VII) 25938 1-benzyl 3-methyl 4-[(4-methoxyphenyl)sulfonyl]-1,3-piperazinedicarboxylate C21H24N2O7S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

The selective protection of piperazine-2-carboxylic acid (I) with tert-butoxycarbonyl anhydride gives the carbamate (II), which is sulfonated with 4-methoxybenzenesulfonyl chloride (II) and triethylamine yielding the sulfonamide (IV). The esterification and simultaneous deprotection of (IV) with SOCl2 and methanol affords the methyl ester (V), which is treated with phosgene and N-benzyl-N-methylamine (VI) to afford the cyclic urea derivative (VII). Finally, this compound is treated with KOH and hydroxylamine in methanol to provide the target hydroxamic acid.

1 De, B.; Natchus, M.G.; Pikul, S.; Almstead, N.G.; Matthews, R.S.; Taiwo, Y.O.; Cheng, M. (The Procter & Gamble Co.); 1,4-Heterocyclic metalloprotease inhibitors. EP 0923563; EP 0925287; WO 9808825; WO 9808827 .
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) 25933 2-piperazinecarboxylic acid; Piperazine-2-carboxylic acid C5H10N2O2 详情 详情
(II) 25934 4-(tert-butoxycarbonyl)-2-piperazinecarboxylic acid C10H18N2O4 详情 详情
(III) 15719 4-methoxybenzenesulfonyl chloride 98-68-0 C7H7ClO3S 详情 详情
(IV) 25935 4-(tert-butoxycarbonyl)-1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylic acid C17H24N2O7S 详情 详情
(V) 25936 methyl 1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylate C13H18N2O5S 详情 详情
(VI) 11969 N-Methyl(phenyl)methanamine; N-Benzyl-N-methylamine; N-Methylbenzylamine 103-67-3 C8H11N 详情 详情
(VII) 25937 methyl 4-[[benzyl(methyl)amino]carbonyl]-1-[(4-methoxyphenyl)sulfonyl]-2-piperazinecarboxylate C22H27N3O6S 详情 详情
Extended Information