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【结 构 式】 
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【药物名称】 【化学名称】N-[3-(4-Cyanobenzamido)-2,2-dimethylnonanoyl]-L-phenylalanine ethyl ester 【CA登记号】 【 分 子 式 】C30H39N3O4 【 分 子 量 】505.66303 |
【开发单位】Nippon Steel (Originator) 【药理作用】PHARMACOLOGICAL TOOLS, Serine Protease Inhibitors |
合成路线1
The condensation of ethyl isobutyrate (I) with ethanal and trimethylsilylamine in THF gives the azetidinone (III), which is treated with 4-cyanobenzoic acid succinimidyl ester (IV) in DMF yielding 3-(4-cyanobenzamido)-2,2-dimethylnonanoic acid (V). Finally, this compound is condensed with L-phenylalanine ethyl ester (VI) by means of DEC and HOBT in dichloromethane.
| 【1】 Iijima, K.; Katada, J.; Yasuda, E.; Uno, I.; Hayashi, Y.; N-[2,2-Dimethyl-3-(N-(4-cyanobenzoyl)amino)nonanoyl]-L-phenylalanine ethyl ester as a stable ester-type inhibitor of chymotrypsin-like serine proteases: Structural requirements for potent inhibition of alpha-chymotrypsin. J Med Chem 1999, 42, 2, 312. |
| 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) | 28650 | ethyl 2-methylpropanoate；ethyl isobutyrate | 97-62-1 | C6H12O2 | 详情 | 详情 |
| (II) | 28655 | Enanthic aldehyde; 1-Heptanal; Heptaldehyde; Oenanthol; Oenanthaldehyde; Enanthal; Oenanthal; Heptyl aldehyde; n-Heptaldehyde; Enanthaldehyde; Enanthole; 1-Heptaldehyde; Heptanaldehyde; n-Heptanal; Oenanthic aldehyde; n-Heptylaldehyde; Heptanal | 111-71-7 | C7H14O | 详情 | 详情 |
| (III) | 28651 | 4-hexyl-3,3-dimethyl-2-azetidinone | C11H21NO | 详情 | 详情 | |
| (IV) | 28652 | 4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzonitrile | C12H8N2O4 | 详情 | 详情 | |
| (V) | 28653 | 3-[(4-cyanobenzoyl)amino]-2,2-dimethylnonanoic acid | C19H26N2O3 | 详情 | 详情 | |
| (VI) | 28654 | (2S)-3-ethoxy-1-phenyl-3-buten-2-amine | C12H17NO | 详情 | 详情 |
Extended Information