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【结 构 式】 
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【分子编号】25292 【品名】(2R)-2-([[4-(5-chloro-2-pyridinyl)-1-piperazinyl]sulfonyl]amino)-3-methylbutyric acid 【CA登记号】 |
【 分 子 式 】C14H21ClN4O4S 【 分 子 量 】376.864 【元素组成】C 44.62% H 5.62% Cl 9.41% N 14.87% O 16.98% S 8.51% |
合成路线1
该中间体在本合成路线中的序号：(V)Treatment of D-valine methyl ester (I) with chlorosulfonic acid and then with phosphorus pentachloride produced valinesulfamoyl cloride (II). This was condensed with N-(5-chloro-2-pyridinyl)piperazine (III) to afford sulfamide (IV). Basic hydrolysis of the methyl ester of (IV) gave carboxylic acid (V), which was further converted to acid chloride (VI) using oxalyl chloride in the presence of DMF. Finally, the title hydroxamic acid was obtained by condensation with N,O-bis(trimethylsilyl)hydroxylamine, followed by desilylation with MeOH.
| 【1】 Castelhano, A.L.; Hendricks, R.T.; Melnick, M.J.; Campbell, J.A.; Walker, K.A.M.; Broka, C.A.; Chen, J.J. (Agouron Pharmaceuticals, Inc.; F. Hoffmann-La Roche AG); Sulfamide-metalloprotease inhibitors. DE 19802350; EP 0958287; US 5998412; WO 9832748 . |
| 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) | 16613 | methyl (2S)-2-amino-3-methylbutanoate | C6H13NO2 | 详情 | 详情 | |
| (II) | 25289 | methyl (2R)-2-[(chlorosulfonyl)amino]-3-methylbutanoate | C6H12ClNO4S | 详情 | 详情 | |
| (III) | 25290 | 1-(5-chloro-2-pyridinyl)piperazine | C9H12ClN3 | 详情 | 详情 | |
| (IV) | 25291 | methyl (2R)-2-([[4-(5-chloro-2-pyridinyl)-1-piperazinyl]sulfonyl]amino)-3-methylbutanoate | C15H23ClN4O4S | 详情 | 详情 | |
| (V) | 25292 | (2R)-2-([[4-(5-chloro-2-pyridinyl)-1-piperazinyl]sulfonyl]amino)-3-methylbutyric acid | C14H21ClN4O4S | 详情 | 详情 | |
| (VI) | 25293 | (2R)-2-([[4-(5-chloro-2-pyridinyl)-1-piperazinyl]sulfonyl]amino)-3-methylbutanoyl chloride | C14H20Cl2N4O3S | 详情 | 详情 |