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【结 构 式】 
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【分子编号】50032 【品名】4-methyl-1-(4-nitrophenyl)-3-oxopentyl acetate 【CA登记号】 |
【 分 子 式 】C14H17NO5 【 分 子 量 】279.29272 【元素组成】C 60.21% H 6.14% N 5.02% O 28.64% |
合成路线1
该中间体在本合成路线中的序号：(V)The hydrolysis of the ketoester (I) with NaOH gives the corresponding ketoacid (II), which is condensed with 4-nitrobenzaldehyde (III) by means of pyridine to yield the hydroxyketone (IV). The reaction of (IV) with acetic anhydride and pyridine affords the acetoxy compound (V), which is dehydrated by means of hot pyridine to provide the enone (VI). The condensation of (VI) with benzyl acetate (VII) by means of LDA gives 3-hydroxy-3-isopropyl-5-(4-nitrophenyl)-4-pentenoic acid benzyl ester (VIII), which is fully hydrogenated with H2 over Pd(OH)2 to yield the amino acid (IX). Finally, (IX) is treated with acetic anhydride to afford the target 5-(4-acetamidophenyl)-3-hydroxy-3-isopropylpentanoic acid intermediate (X).
| 【1】 Deering, C.F.; et al.; Application of the Schöpf method to optimization of the synthesis of 3-[2-(p-N-acetylaminophenyl)ethyl]-3-hydroxy-4-methylpentanoic acid: Simultaneous reduction of three functional groups to maximine yield and throughput. Org Process Res Dev 2000, 4, 6, 596. |
| 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) | 43331 | methyl 4-methyl-3-oxopentanoate | 42558-54-3 | C7H12O3 | 详情 | 详情 |
| (II) | 50030 | 4-methyl-3-oxopentanoic acid | C6H10O3 | 详情 | 详情 | |
| (III) | 18184 | 4-Nitrobenzaldehyde | 555-16-8 | C7H5NO3 | 详情 | 详情 |
| (IV) | 50031 | 1-hydroxy-4-methyl-1-(4-nitrophenyl)-3-pentanone | C12H15NO4 | 详情 | 详情 | |
| (V) | 50032 | 4-methyl-1-(4-nitrophenyl)-3-oxopentyl acetate | C14H17NO5 | 详情 | 详情 | |
| (VI) | 50033 | (E)-4-methyl-1-(4-nitrophenyl)-1-penten-3-one | C12H13NO3 | 详情 | 详情 | |
| (VII) | 35457 | benzyl acetate | 140-11-4 | C9H10O2 | 详情 | 详情 |
| (VIII) | 50034 | benzyl (E)-3-hydroxy-3-isopropyl-5-(4-nitrophenyl)-4-pentenoate | C21H23NO5 | 详情 | 详情 | |
| (IX) | 50035 | 3-(4-aminophenethyl)-3-hydroxy-4-methylpentanoic acid | C14H21NO3 | 详情 | 详情 | |
| (X) | 50036 | 3-[4-(acetamido)phenethyl]-3-hydroxy-4-methylpentanoic acid | C16H23NO4 | 详情 | 详情 |