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【结 构 式】 
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【药物名称】 【化学名称】N-(2,4-Dichlorobenzoyl)-N-(3-nitrobenzyl)-L-phenylalanine 【CA登记号】478294-73-4 【 分 子 式 】C23H18Cl2N2O5 【 分 子 量 】473.31631 |
【开发单位】Shire BioChem (Originator) 【药理作用】Anti-Hepatitis C Virus Drugs, Anti-Hepatitis Virus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, RNA-Directed RNA Polymerase (NS5B) Inhibitors |
合成路线1
Acylation of L-phenylalanine tert-butyl ester (I) with 2,4-dichlorobenzoyl chloride (II) provides the corresponding amide (III). This is then N-alkylated with 3-nitrobenzyl bromide (IV) in the presence of NaH to yield (V). The tert-butyl ester group of (V) is finally cleaved with trifluoroacetic acid to furnish the target carboxylic acid. (1-3)
| 【1】 Chan, L.; Reddy, J.; Proulx, M.; Das, S.K.; Pereira, O.; Wang, W.; Siddiqui, A.; Yannopoulos, C.G.; Poisson, C.; Turcotte, N.; Drouin, A.; Alaoui-Ismaili, M.H.; Bethell, R.; Hamel, M.; L'Heureux, L.; Bilimoria, D.; Nguyen-Ba, N.; Identification of N,N-disubstituted phenylalanines as a novel class of inhibitors of hepatitis C NS5B polymerase. J Med Chem 2003, 46, 8, 1283. |
| 【2】 Proulx, M.; Chan, L.; Reddy, T.J.; Das, S.K.; Pereira, O.Z.; Identification of a novel class of inhibitors of hepatitis C NS5B polymerase. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 40. |
| 【3】 Pereira, O.Z.; Wang, W.; Siddiqui, M.A.; Bedard, J.; Nguyen Ba, N.; Chan, C.K.L.; Das, S.K.; Shuttleworth, S. (Shire BioChem Inc.); Cpds. and methods for the treatment or prevention of flavivirus infections. US 2003229053; WO 02100846 . |
| 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) | 60837 | tert-butyl (2S)-2-amino-3-phenylpropanoate | C13H19NO2 | 详情 | 详情 | |
| (II) | 35131 | 2,4-dichlorobenzoyl chloride; 2,4-Dichlorophenacylchloride | 89-75-8 | C7H3Cl3O | 详情 | 详情 |
| (III) | 64057 | 1,1-dimethylethyl 2-{[(2,4-dichlorophenyl)carbonyl]amino}-3-phenylpropanoate | C20H21Cl2NO3 | 详情 | 详情 | |
| (IV) | 19636 | 1-(bromomethyl)-3-nitrobenzene | 3958-57-4 | C7H6BrNO2 | 详情 | 详情 |
| (V) | 64058 | 1,1-dimethylethyl 2-{[(2,4-dichlorophenyl)carbonyl][(3-nitrophenyl)methyl]amino}-3-phenylpropanoate | C27H26Cl2N2O5 | 详情 | 详情 |
Extended Information