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【结 构 式】 
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【分子编号】18469 【品名】benzyl (2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoate 【CA登记号】 |
【 分 子 式 】C23H29NO4 【 分 子 量 】383.4876 【元素组成】C 72.04% H 7.62% N 3.65% O 16.69% |
合成路线1
该中间体在本合成路线中的序号：(II)N-Boc-D-(3-phenylpropyl)glycine (I) was esterified to benzyl ester (II), and then, tert-butoxycarbonyl group was cleaved by acidic treatment to give amine (III). This was coupled with N-Boc-2-aminoisobutyric acid (IV) in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to afford dipeptide ester (V), from which the benzyl ester group was removed by hydrogenolysis in the presence of Pd/C. The resulting acid (VI) was condensed with 1-(2-nitrophenyl)piperazine (VII) in the presence of EDC and HOBt to produce piperazide (VIII). Subsequent reduction of the nitro group by hydrogenation in the presence of Raney-Ni gave aniline (IX), which was treated with 2-propanesulfonyl chloride (X) to yield sulfonamide (XI). Finally, the tert-butoxycarbonyl protecting group was removed by treatment either with HCl in EtOAc or with trifluoroacetic acid to afford the target compound as the hydrochloride or the trifluoroacetate salt, respectively.
| 【1】 Barakat, K.J.; Cheng, K.; Chan, W.W.; Butler, B.S.; Jacks, T.M.; Schleim, K.D.; Hora, D.F. Jr.; Hickey, G.J.; Smith, R.G.; Patchett, A.A.; Nargund, R.P.; Synthesis and biological activities of phenyl piperazine-based peptidomimetic growth hormone secretagogues. Bioorg Med Chem Lett 1998, 8, 11, 1431. |
| 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) | 18468 | (2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoic acid | C16H23NO4 | 详情 | 详情 | |
| (II) | 18469 | benzyl (2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoate | C23H29NO4 | 详情 | 详情 | |
| (III) | 18470 | benzyl (2R)-2-amino-5-phenylpentanoate | C18H21NO2 | 详情 | 详情 | |
| (IV) | 18471 | N-(tert-butoxycarbonyl)-2-methylalanine | 30992-29-1 | C9H17NO4 | 详情 | 详情 |
| (V) | 18472 | benzyl (2R)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)-5-phenylpentanoate | C27H36N2O5 | 详情 | 详情 | |
| (VI) | 18473 | (2R)-2-([2-[(tert-butoxycarbonyl)amino]-2-methylpropanoyl]amino)-5-phenylpentanoic acid | C20H30N2O5 | 详情 | 详情 | |
| (VII) | 18474 | 1-(2-nitrophenyl)piperazine | C10H13N3O2 | 详情 | 详情 | |
| (VIII) | 18475 | tert-butyl 1,1-dimethyl-2-[((1R)-1-[[4-(2-nitrophenyl)-1-piperazinyl]carbonyl]-4-phenylbutyl)amino]-2-oxoethylcarbamate | C30H41N5O6 | 详情 | 详情 | |
| (IX) | 18476 | tert-butyl 2-[((1R)-1-[[4-(2-aminophenyl)-1-piperazinyl]carbonyl]-4-phenylbutyl)amino]-1,1-dimethyl-2-oxoethylcarbamate | C30H43N5O4 | 详情 | 详情 | |
| (X) | 18477 | 2-propanesulfonyl chloride | 10147-37-2 | C3H7ClO2S | 详情 | 详情 |
| (XI) | 18478 | tert-butyl 2-([(1R)-1-[(4-[2-[(isopropylsulfonyl)amino]phenyl]-1-piperazinyl)carbonyl]-4-phenylbutyl]amino)-1,1-dimethyl-2-oxoethylcarbamate | C33H49N5O6S | 详情 | 详情 |