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【结 构 式】 
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【分子编号】44950 【品名】(2S)-1-[(2S,5S,8S,11S)-11-[2-(tert-butoxy)-2-oxoethyl]-8-[3-(tert-butoxy)-3-oxopropyl]-2,5-diisopropyl-15,15-dimethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl]-2-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C37H63N5O12 【 分 子 量 】769.93372 【元素组成】C 57.72% H 8.25% N 9.1% O 24.94% |
合成路线1
该中间体在本合成路线中的序号：(XII)Racemic allylglycine (I) was protected as the N-Boc derivative (II) and then converted to the Weinreb amide (III) by treatment with N,O-dimethylhydroxylamine and BOP. Reduction of (III) with LiAlH4 afforded aldehyde (IV), which, upon treatment with acetone cyanohydrin (V), furnished the corresponding hydroxy nitrile (VI). Acid hydrolysis of the nitrile (VI) with concomitant Boc group deprotection provided hydroxy acid (VII), which was further reprotected as the N-Boc derivative (VIII). Coupling of hydroxy acid (VIII) with allylamine (IX) yielded amide (X). After Boc group cleavage with HCl in dioxan, the resulting amine (XI) was coupled with pentapeptide (XII) (obtained using a peptide synthesizer under standard conditions), to give the alpha-hydroxyamide (XIII).
| 【1】 Hu, Z.; Han, W.; Jiang, X.; Decicco, C.P.; alpha-Ketoamides, alpha-ketoesters and alpha-diketones as HCV NS3 protease inhibitors. Bioorg Med Chem Lett 2000, 10, 8, 711. |
| 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) | 44941 | 2-amino-4-pentenoic acid | 7685-44-1 | C5H9NO2 | 详情 | 详情 |
| (II) | 44942 | 2-[(tert-butoxycarbonyl)amino]-4-pentenoic acid | C10H17NO4 | 详情 | 详情 | |
| (III) | 44943 | tert-butyl 1-[[methoxy(methyl)amino]carbonyl]-3-butenylcarbamate | C12H22N2O4 | 详情 | 详情 | |
| (IV) | 44944 | tert-butyl 1-formyl-3-butenylcarbamate | C10H17NO3 | 详情 | 详情 | |
| (V) | 18029 | Acetone cyanohydrin; 2-Hydroxy-2-methylpropanenitrile; 2-Hydroxy-2-methylpropionitrile; 2-Hydroxyisobutyronitrile; 2-Methyllactonitrile; alpha-Hydroxyisobutyronitrile | 75-86-5 | C4H7NO | 详情 | 详情 |
| (VI) | 44945 | tert-butyl 1-[cyano(hydroxy)methyl]-3-butenylcarbamate | C11H18N2O3 | 详情 | 详情 | |
| (VII) | 44946 | 3-amino-2-hydroxy-5-hexenoic acid | C6H11NO3 | 详情 | 详情 | |
| (VIII) | 44947 | 3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-hexenoic acid | C11H19NO5 | 详情 | 详情 | |
| (IX) | 13672 | Allylamine; 2-Propen-1-amine | 107-11-9 | C3H7N | 详情 | 详情 |
| (X) | 44948 | tert-butyl 1-[2-(allylamino)-1-hydroxy-2-oxoethyl]-3-butenylcarbamate | C14H24N2O4 | 详情 | 详情 | |
| (XI) | 44949 | N-allyl-3-amino-2-hydroxy-5-hexenamide | C9H16N2O2 | 详情 | 详情 | |
| (XII) | 44950 | (2S)-1-[(2S,5S,8S,11S)-11-[2-(tert-butoxy)-2-oxoethyl]-8-[3-(tert-butoxy)-3-oxopropyl]-2,5-diisopropyl-15,15-dimethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl]-2-pyrrolidinecarboxylic acid | C37H63N5O12 | 详情 | 详情 | |
| (XIII) | 44951 | tert-butyl (4S)-5-[[(1S)-1-([[(1S)-1-([(2S)-2-[([1-[2-(allylamino)-1-hydroxy-2-oxoethyl]-3-butenyl]amino)carbonyl]pyrrolidinyl]carbonyl)-2-methylpropyl]amino]carbonyl)-2-methylpropyl]amino]-4-([(2S)-4-(tert-butoxy)-2-[(tert-butoxycarbonyl)amino]-4-o | C46H77N7O13 | 详情 | 详情 |