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【结 构 式】 
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【分子编号】40207 【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate 【CA登记号】 |
【 分 子 式 】C12H23NO5 【 分 子 量 】261.31836 【元素组成】C 55.16% H 8.87% N 5.36% O 30.61% |
合成路线1
该中间体在本合成路线中的序号：(VI)Isoxazolin-5-one (III) was synthesized from ethyl propiolate (I) via ethyl malonaldehyde oxime (II) by a known method. Treatment of N-Boc-L-serine (IV) with N,N-dimethylformamide di-tert-butylacetal (V) in refluxing benzene produced Boc-serine tert-butyl ester (VI) along with a small amount of O-formyl derivative, which was separated by column chromatography. Mitsunobu coupling of isoxazolinone (III) with serine derivative (VI) employing diisopropyl azodicarboxylate (DIAD) and triphenylphosphine afforded the protected O-isoxazolyl serine (VII). The protecting groups of (VII) were finally removed by treatment with trifluoroacetic acid.
| 【1】 Ikegami, F.; et al.; Synthesis and pharmacological activity of O-(5-isoxazolyl)-L-serine. Chem Pharm Bull 2000, 48, 2, 278. |
| 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) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (II) | 40205 | ethyl 3-(hydroxyimino)propanoate | C5H9NO3 | 详情 | 详情 | |
| (III) | 40206 | 5(4H)-isoxazolone | C3H3NO2 | 详情 | 详情 | |
| (IV) | 20126 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid | C8H15NO5 | 详情 | 详情 | |
| (V) | 21059 | N-[di(tert-butoxy)methyl]-N,N-dimethylamine; di(tert-butoxy)-N,N-dimethylmethanamine | 36805-97-7 | C11H25NO2 | 详情 | 详情 |
| (VI) | 40207 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate | C12H23NO5 | 详情 | 详情 | |
| (VII) | 40208 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(5-isoxazolyloxy)propanoate | C15H24N2O6 | 详情 | 详情 |