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【结 构 式】 
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【分子编号】30456 【品名】4-[[(1S)-1-benzyl-2-(2-hydroxyethoxy)ethyl]amino]-N-[(1S)-2-(4-ethyl-1-piperidinyl)-1-(4-nitrobenzyl)-2-oxoethyl]-3-pyridinesulfonamide 【CA登记号】 |
【 分 子 式 】C32H41N5O7S 【 分 子 量 】639.77304 【元素组成】C 60.08% H 6.46% N 10.95% O 17.51% S 5.01% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The condensation of N-(tert-butoxycarbonyl)-4-nitro-L-phenylalanine (I) with 4-ethylpiperiine (II) by means of diisopropylethylamine (DIEA) in dichloromethane gives the corresponding protected piperidide (III), which is treated with TFA to eliminate the carbamate group yielding (IV). The sulfonation of (IV) with 4-chloropyridine-3-sulfonyl chloride (V) by means of DIEA in dichloromethane affords the sulfonamide (VI), which is condensed with 2-(2(S)-amino-3-phenylpropoxy)ethanol (VII) by means of DIEA in ethanol giving the intermediate (VIII). Finally, the reduction of the nitro group of (VIII) with H2 over Pd/C in methanol affords the target compound.
| 【1】 Brundish, D.E.; Brown, L.N.; Le Grand, D.M.; Menear, K.A.; Smith, G.P.; Allen, M.C.; Butler, P.I.; Cockroft, X.-L.; Matthews, I.T.W.; Walker, C.V.; Wathey, W.B. (Novartis AG); Thrombin inhibitors. WO 9746553 . |
| 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) | 28516 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-nitrophenyl)propionic acid | C14H18N2O6 | 详情 | 详情 | |
| (II) | 30451 | 4-ethylpiperidine | C7H15N | 详情 | 详情 | |
| (III) | 30452 | tert-butyl (1S)-2-(4-ethyl-1-piperidinyl)-1-(4-nitrobenzyl)-2-oxoethylcarbamate | C21H31N3O5 | 详情 | 详情 | |
| (IV) | 30453 | (2S)-2-amino-1-(4-ethyl-1-piperidinyl)-3-(4-nitrophenyl)-1-propanone | C16H23N3O3 | 详情 | 详情 | |
| (V) | 28521 | 4-chloro-3-pyridinesulfonyl chloride | C5H3Cl2NO2S | 详情 | 详情 | |
| (VI) | 30454 | 4-chloro-N-[(1S)-2-(4-ethyl-1-piperidinyl)-1-(4-nitrobenzyl)-2-oxoethyl]-3-pyridinesulfonamide | C21H25ClN4O5S | 详情 | 详情 | |
| (VII) | 30455 | 2-[[(2S)-2-amino-3-phenylpropyl]oxy]-1-ethanol | C11H17NO2 | 详情 | 详情 | |
| (VIII) | 30456 | 4-[[(1S)-1-benzyl-2-(2-hydroxyethoxy)ethyl]amino]-N-[(1S)-2-(4-ethyl-1-piperidinyl)-1-(4-nitrobenzyl)-2-oxoethyl]-3-pyridinesulfonamide | C32H41N5O7S | 详情 | 详情 |