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【结 构 式】 
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【分子编号】30888 【品名】(2S)-2-[([(2S)-1-[(benzyloxy)carbonyl]pyrrolidinyl]carbonyl)amino]-4-methylpentanoic acid 【CA登记号】61596-47-2 |
【 分 子 式 】C19H26N2O5 【 分 子 量 】362.42592 【元素组成】C 62.97% H 7.23% N 7.73% O 22.07% |
合成路线1
该中间体在本合成路线中的序号：(VII)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 |