|
【结 构 式】 
|
【药物名称】 【化学名称】L-Prolyl-L-leucyl-2,2-(diethyl)glycinamide 【CA登记号】 【 分 子 式 】C17H32N4O3 【 分 子 量 】340.46959 |
【开发单位】McMaster University (Originator), University of Minnesota (Originator) 【药理作用】Antidepressants, Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
This compound has been obtained by two different ways: 1) The reaction of 2-(tert-butoxycarbonyl)-2-ethylbutyric acid (I) with ammonia, EDC and HOBT gives the amide (II), which is deprotected with 4N HCl and condensed with N-(tert-butoxycarbonyl)-L-leucine (III) by means of EDC and HOBT yielding the dipeptide (IV). The deprotection of (IV) with HCl and condensation with 1-(tert-butoxycarbonyl)-L-proline pentafluorophenyl ester (V) affords the protected tripeptide (VI), which is finally deprotected with 4N HCl. 2) The deprotection of amide (II) with HCl followed by condensation with N-(benzyloxcarbonyl)-L-prolyl-L-leucine (VII) gives the protected tripeptide (VIII), which is deprotected by hydrogenation with H2 over Pd/C.
| 【1】 Evans, M.C.; et al.; Synthesis and dopamine receptor modulating activity of novel peptidomimetics of L-prolyl-L-leucyl-glycinamide featuring alpha,alpha-disubstituted amino acids. J Med Chem 1999, 42, 8, 1441. |
| 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) | 30883 | 2-[(tert-butoxycarbonyl)amino]-2-ethylbutyric acid | C11H21NO4 | 详情 | 详情 | |
| (II) | 30884 | tert-butyl 1-(aminocarbonyl)-1-ethylpropylcarbamate | C11H22N2O3 | 详情 | 详情 | |
| (III) | 23663 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine | C11H21NO4 | 详情 | 详情 | |
| (IV) | 30885 | tert-butyl (1S)-1-([[1-(aminocarbonyl)-1-ethylpropyl]amino]carbonyl)-3-methylbutylcarbamate | C17H33N3O4 | 详情 | 详情 | |
| (V) | 30886 | 1-(tert-butyl) 2-(2,3,4,5,6-pentafluorophenyl) (2S)-1,2-pyrrolidinedicarboxylate | C16H16F5NO4 | 详情 | 详情 | |
| (VI) | 30887 | tert-butyl (2S)-2-([[(1S)-1-([[1-(aminocarbonyl)-1-ethylpropyl]amino]carbonyl)-3-methylbutyl]amino]carbonyl)-1-pyrrolidinecarboxylate | C22H40N4O5 | 详情 | 详情 | |
| (VII) | 30888 | (2S)-2-[([(2S)-1-[(benzyloxy)carbonyl]pyrrolidinyl]carbonyl)amino]-4-methylpentanoic acid | 61596-47-2 | C19H26N2O5 | 详情 | 详情 |
| (VIII) | 30889 | benzyl (2S)-2-([[(1S)-1-([[1-(aminocarbonyl)-1-ethylpropyl]amino]carbonyl)-3-methylbutyl]amino]carbonyl)-1-pyrrolidinecarboxylate | C25H38N4O5 | 详情 | 详情 |