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【结 构 式】 
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【分子编号】56727 【品名】(2R)-2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propanoic acid 【CA登记号】 |
【 分 子 式 】C17H13ClN2O4 【 分 子 量 】344.754 【元素组成】C 59.23% H 3.8% Cl 10.28% N 8.13% O 18.56% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The reaction of (S)(-)-lactic acid methyl ester (I) with Ts-Cl and TEA in dichloromethane gives the corresponding tosylate (II), which is condensed with 4-(benzyloxy)phenol (III) by means of NaH in DMF to yield (R)(+)-2-[4-(benzyloxy)phenoxy]propionic acid methyl ester (IV). The hydrogenolysis of the benzyl group of (IV) with H2 over Pd/C in ethyl acetate affords the 4-hydroxyphenoxy compound (V), which is condensed with 2,7-dichloroquinoxaline (VI) by means of K2CO3 in refluxing acetone, provides the ester precursor (VII). The hydrolysis of (VII) with KOH in THF/water, followed by acidification with HCl, gives the chiral propionic acid (VIII), which is finally converted into its sodium salt with NaOH in water.
| 【1】 Behrens, C.H.; Dusak, B.A.; Harrison, B.A.; Orwat, M.J. (Bristol-Myers Squibb Co.); (2-Quinoxalinyloxy)phenoxypropanoic acids and related derivs. as anticancer agents. WO 9413647 . |
| 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) | 17075 | propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate | 27871-49-4 | C4H8O3 | 详情 | 详情 |
| (II) | 56722 | methyl (2S)-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate | C11H14O5S | 详情 | 详情 | |
| (III) | 18956 | 4-(Benzyloxy)phenol; 4-Benzyloxyphenol | 103-16-2 | C13H12O2 | 详情 | 详情 |
| (IV) | 56723 | methyl (2R)-2-[4-(benzyloxy)phenoxy]propanoate | C17H18O4 | 详情 | 详情 | |
| (V) | 56724 | methyl (2R)-2-(4-hydroxyphenoxy)propanoate | C10H12O4 | 详情 | 详情 | |
| (VI) | 56725 | 2,7-dichloroquinoxaline | 59489-31-5 | C8H4Cl2N2 | 详情 | 详情 |
| (VII) | 56726 | methyl (2R)-2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propanoate | C18H15ClN2O4 | 详情 | 详情 | |
| (VIII) | 56727 | (2R)-2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propanoic acid | C17H13ClN2O4 | 详情 | 详情 |