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【结 构 式】 
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【药物名称】 【化学名称】N2-[2(S)-(3,5-Difluorophenyl)-2-hydroxyacetyl]-N1-[1(S)-(hydroxymethyl)-4-phenylbutyl]-L-alaninamide 【CA登记号】 【 分 子 式 】C22H26F2N2O4 【 分 子 量 】420.46032 |
【开发单位】Elan (Originator), Lilly (Originator) 【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, gamma-Secretase Inhibitors |
合成路线1
Coupling between methyl 2-amino-5-phenylpentanoate (I) and N-Boc-alanine (II) affords dipeptide (III). Deprotection of (III) with trifluoroacetic acid yields amine (IV), which is then acylated with (S)-3,5-difluoromandelic acid (V), producing amide (VI). Finally, ester group reduction using LiBH4 leads to the desired alcohol.
| 【1】 Garofalo, A.W.; et al.; A series of C-terminal amino alcohol dipeptide Abeta inhibitors. 28th Natl Med Chem Symp (June 8 2002, San Diego) 2002, Abst 11. |
| 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) | 58436 | methyl (2S)-2-amino-5-phenylpentanoate | C12H17NO2 | 详情 | 详情 | |
| (II) | 26450 | Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid | 15761-38-3 | C8H15NO4 | 详情 | 详情 |
| (III) | 58437 | methyl (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl}amino)-5-phenylpentanoate | C20H30N2O5 | 详情 | 详情 | |
| (IV) | 58438 | methyl (2S)-2-{[(2S)-2-aminopropanoyl]amino}-5-phenylpentanoate | C15H22N2O3 | 详情 | 详情 | |
| (V) | 58439 | (2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoic acid | C8H6F2O3 | 详情 | 详情 | |
| (VI) | 58440 | methyl (2S)-2-[((2S)-2-{[(2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoyl]amino}propanoyl)amino]-5-phenylpentanoate | C23H26F2N2O5 | 详情 | 详情 |
Extended Information