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【结 构 式】 
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【分子编号】18172 【品名】(2R)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanamide 【CA登记号】 |
【 分 子 式 】C24H35NO2S 【 分 子 量 】401.61344 【元素组成】C 71.78% H 8.78% N 3.49% O 7.97% S 7.98% |
合成路线1
该中间体在本合成路线中的序号：(VIII)2-Naphtalenethiol (I) was treated with ethyl 4-bromobutyrate (II) and NaH to give thioether (III). Alkylation of (III) with isobutyl iodide (IV) in the presence of LDA afforded racemic (V), which was then hydrolyzed to the acid (VI) on treatment with litium hydroxide. Coupling of racemic acid (VI) with (S)-leucinol (VII) yielded a mixture of diastereomeric amides, which were separated by column chromatography. Diastereoisomer (VIII) was oxidized with m-chloroperbenzoic acid to give sulfone (IX), and was further oxidized with DMSO and sulfur trioxide-pyridine complex to produce the target aldehyde.
| 【1】 Chatterjee, S.; et al.; Nonpeptidic inhibitors of recombinant human calpain; I. Bioorg Med Chem Lett 1997, 7, 3, 287-290. |
| 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) | 15234 | 2-Naphthalenethiol; 2-Naphthylhydrosulfide | 91-60-1 | C10H8S | 详情 | 详情 |
| (II) | 11263 | ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate | 2969-81-5 | C6H11BrO2 | 详情 | 详情 |
| (III) | 18167 | ethyl 4-(2-naphthylsulfanyl)butanoate | C16H18O2S | 详情 | 详情 | |
| (IV) | 18168 | 1-iodo-2-methylpropane | 513-38-2 | C4H9I | 详情 | 详情 |
| (V) | 18169 | ethyl 4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanoate | C20H26O2S | 详情 | 详情 | |
| (VI) | 18170 | 4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanoic acid | C18H22O2S | 详情 | 详情 | |
| (VII) | 18171 | L-(+)-leucinol; (S)-2-amino-4-methyl-1-pentanol; (2S)-2-amino-4-methyl-1-pentanol | 7533-40-6 | C6H15NO | 详情 | 详情 |
| (VIII) | 18172 | (2R)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanamide | C24H35NO2S | 详情 | 详情 | |
| (IX) | 18173 | (2R)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-4-methyl-2-[2-(2-naphthylsulfonyl)ethyl]pentanamide | C24H35NO4S | 详情 | 详情 |