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【结 构 式】 
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【药物名称】 【化学名称】2(S)-(2-Hydroxy-5-nitrobenzylamino)-N-isopentyl-3-phenylpropionamide
【CA登记号】 【 分 子 式 】C21H27N3O4 【 分 子 量 】385.46704 |
【开发单位】Millennium (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, Cell Adhesion Inhibitors, Integrin alpha4beta7 (LPAM-1) Antagonists |
合成路线1
Coupling of N-Boc-phenylalanine (I) with amine (II) by means of HBTU and DIEA provides amide (III), whose Boc group is removed by treatment with HCl in dioxane to afford amine hydrochloride (IV). Finally, the target compound is obtained by reductive amination between amine (IV) and aldehyde (V) in MeOH in the presence of NaCNBH3.
| 【1】 Harriman, G.C.B.; Cochran, N.A.; Gallant, D.; Briskin, M.J.; Schwender, C.F.; Cell adhesion antagonists: Synthesis and evaluation of a novel series of phenylalanine based inhibitors. Bioorg Med Chem Lett 2000, 10, 14, 1497. |
| 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) | 12874 | (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine | 13734-34-4 | C14H19NO4 | 详情 | 详情 |
| (II) | 46226 | isopentylamine; 3-methyl-1-butanamine | C5H13N | 详情 | 详情 | |
| (III) | 46225 | tert-butyl (1S)-1-benzyl-2-(isopentylamino)-2-oxoethylcarbamate | C19H30N2O3 | 详情 | 详情 | |
| (IV) | 46227 | (2S)-2-amino-N-isopentyl-3-phenylpropanamide | C14H22N2O | 详情 | 详情 | |
| (V) | 42307 | 2-hydroxy-5-nitrobenzaldehyde；5-nitrosalicylaldehyde | 97-51-8 | C7H5NO4 | 详情 | 详情 |
Extended Information