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【结 构 式】 
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【分子编号】28452 【品名】tert-butyl 2-((Z)-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]phenyl]methylidene)-1-hydrazinecarboxylate 【CA登记号】 |
【 分 子 式 】C22H26N6O2 【 分 子 量 】406.48768 【元素组成】C 65.01% H 6.45% N 20.67% O 7.87% |
合成路线1
该中间体在本合成路线中的序号：(V)Cycloaddition of sodium azide to 4-formylbenzonitrile (I) yielded tetrazole (II), which was protected with 2-phenylpropene (III) in the presence of methanesulfonic acid to give (IV). Subsequent condensation of (IV) with tert-butyl carbazate afforded hydrazone (V), which was further reduced to the benzylhydrazine (VI) employing NaBH3CN and p-toluenesulfonic acid. Opening of the trifluoroacetyl-protected epoxide (VII) with hydrazine (VI) gave hydrazinoalcohol (VIII). After hydrolysis of the trifluoroacetamide group of (VIII) with K2CO3, the resulting amine (IX) was coupled with N-methoxycarbonyl-L-tert-leucine (X) by means of EDC and HOBt to provide amide (XI).
| 【1】 Fassler, A.; Bold, G.; Capraro, H.-G.; Lang, M.; Khanna, S.C. (Novartis AG); Antivirally active heterocyclic azahexane derivs.. EP 0900210; JP 1999511177; US 5849911; WO 9740029 . |
| 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) | 17552 | 4-formylbenzonitrile; 4-Cyanobenzaldehyde | 105-07-7 | C8H5NO | 详情 | 详情 |
| (II) | 28449 | 4-(2H-1,2,3,4-tetraazol-5-yl)benzaldehyde | 74815-22-8 | C8H6N4O | 详情 | 详情 |
| (III) | 28450 | 1-isopropenylbenzene | 98-83-9 | C9H10 | 详情 | 详情 |
| (IV) | 28451 | 4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]benzaldehyde | C17H16N4O | 详情 | 详情 | |
| (V) | 28452 | tert-butyl 2-((Z)-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]phenyl]methylidene)-1-hydrazinecarboxylate | C22H26N6O2 | 详情 | 详情 | |
| (VI) | 28453 | tert-butyl 2-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]benzyl]-1-hydrazinecarboxylate | C22H28N6O2 | 详情 | 详情 | |
| (VII) | 28454 | 2,2,2-trifluoro-N-[(1S)-1-[(2R)oxiranyl]-2-phenylethyl]acetamide | C12H12F3NO2 | 详情 | 详情 | |
| (VIII) | 28455 | tert-butyl 2-[(2S,3S)-2-hydroxy-4-phenyl-3-[(2,2,2-trifluoroacetyl)amino]butyl]-2-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]benzyl]-1-hydrazinecarboxylate | C34H40F3N7O4 | 详情 | 详情 | |
| (IX) | 28456 | tert-butyl 2-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyl]-2-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]benzyl]-1-hydrazinecarboxylate | C32H41N7O3 | 详情 | 详情 | |
| (X) | 23447 | (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutyric acid | C8H15NO4 | 详情 | 详情 | |
| (XI) | 28457 | tert-butyl (5S,6S,9S)-6-benzyl-9-(tert-butyl)-5-hydroxy-3-[4-[2-(1-methyl-1-phenylethyl)-2H-1,2,3,4-tetraazol-5-yl]benzyl]-8,11-dioxo-12-oxa-2,3,7,10-tetraazatridecan-1-oate | C40H54N8O6 | 详情 | 详情 |