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【结 构 式】 
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【药物名称】VB-19038 【化学名称】N-(Cyclopentylmethyl)-N-[3-[3,5(S)-dibenzyl-2-oxoimidazolidin-1-yl]-2(S)-hydroxypropyl]-4-methoxybenzenesulfonamide 【CA登记号】 【 分 子 式 】C33H41N3O5S 【 分 子 量 】591.77582 |
【开发单位】Vertex (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, HIV Protease Inhibitors |
合成路线1
N-Cbz-L-Phenylalaninol (I) was converted to mesylate (II) on treatment with methanesulfonyl chloride and Et3N, and then treated with benzylamine (III) in the presence of NaI to give (IV). Subsequent deprotection of the Cbz group of (IV) with HBr in AcOH afforded diamine (V), which was treated with carbonyl diimidazole to produce the cyclic urea (VI). Finally, condensation with the epoxisulfonamide (VII) in the presence of NaH in DMF provided the target compound.
| 【1】 Salituro, F.G.; Baker, C.T.; Court, J.J.; Deininger, D.D.; Kim, E.E.; Li, B.; Novak, P.M.; Rao, B.G.; Pazhanisamy, S.; Porter, M.D.; Schairer, W.C.; Tung, R.D.; Design and synthesis of novel conformationally restricted HIV protease inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3637. |
| 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) | 16585 | benzyl N-[(1S)-1-benzyl-2-hydroxyethyl]carbamate | C17H19NO3 | 详情 | 详情 | |
| (II) | 20158 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropyl methanesulfonate | C18H21NO5S | 详情 | 详情 | |
| (III) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (IV) | 20160 | benzyl (1S)-1-benzyl-2-(benzylamino)ethylcarbamate | C24H26N2O2 | 详情 | 详情 | |
| (V) | 20161 | (2S)-N(1)-benzyl-3-phenyl-1,2-propanediamine; N-[(2S)-2-amino-3-phenylpropyl]-N-benzylamine | C16H20N2 | 详情 | 详情 | |
| (VI) | 20162 | (4S)-1,4-dibenzyl-2-imidazolidinone | C17H18N2O | 详情 | 详情 | |
| (VII) | 20163 | N-(cyclopentylmethyl)-4-methoxy-N-[(2R)oxiranylmethyl]benzenesulfonamide | C16H23NO4S | 详情 | 详情 |