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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information