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【结 构 式】 
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【分子编号】51651 【品名】ethyl (E,3S)-3-[(tert-butoxycarbonyl)amino]-5-phenyl-1-pentene-1-sulfonate 【CA登记号】 |
【 分 子 式 】C18H27NO5S 【 分 子 量 】369.48212 【元素组成】C 58.51% H 7.37% N 3.79% O 21.65% S 8.68% |
合成路线1
该中间体在本合成路线中的序号：(III)The Horner-Wadsworth-Emmons olefination of N-(tert-butoxycarbonyl)-L-homophenylalaninal (I) with phosphonate (II) by means of NaH in THF gives the vinylsulfonate (III), which is treated with tetrabutylammonium iodide and triphosgene to yield the sulfonyl chloride (IV). The reaction of (IV) with O-benzylhydroxylamine in dichloromethane affords the N-sulfonylhydroxylamine derivative (V), which is deprotected with TFA in dichloromethane, providing compound (VI) with a free amino group. Finally, this compound is condensed with N-(morpholin-4-ylcarbonyl)-L-phenylalanine (VII) by means of HOBt, EDC and NMM in DMF, giving rise to the target amide.
| 【1】 Roush, W.R.; et al.; Potent second generation vinyl sulfonamide inhibitors of the trypanosomal cysteine protease cruzain. Bioorg Med Chem Lett 2001, 11, 20, 2759. |
| 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) | 23624 | diethyl (phenylsulfonyl)methylphosphonate | C11H17O5PS | 详情 | 详情 | |
| (II) | 51650 | ethyl dimethoxy(oxo)phosphoranesulfonate | C4H11O6PS | 详情 | 详情 | |
| (III) | 51651 | ethyl (E,3S)-3-[(tert-butoxycarbonyl)amino]-5-phenyl-1-pentene-1-sulfonate | C18H27NO5S | 详情 | 详情 | |
| (IV) | 51652 | tert-butyl (1S,2E)-3-(chlorosulfonyl)-1-phenethyl-2-propenylcarbamate | C16H22ClNO4S | 详情 | 详情 | |
| (V) | 51653 | tert-butyl (1S,2E)-3-[[(benzyloxy)amino]sulfonyl]-1-phenethyl-2-propenylcarbamate | C23H30N2O5S | 详情 | 详情 | |
| (VI) | 51654 | (E,3S)-3-amino-N-(benzyloxy)-5-phenyl-1-pentene-1-sulfonamide | C18H22N2O3S | 详情 | 详情 | |
| (VII) | 23627 | (2S)-2-[(4-morpholinylcarbonyl)amino]-3-phenylpropionic acid | C14H18N2O4 | 详情 | 详情 |