methyl (2R)-2-(4-hydroxyphenoxy)propanoate -Drug Synthesis Database

【结构式】

【分子编号】56724

【品名】methyl (2R)-2-(4-hydroxyphenoxy)propanoate

【CA登记号】

【分子式】C₁₀H₁₂O₄

【分子量】196.20288

【元素组成】C 61.22% H 6.16% O 32.62%

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：(V)

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.

参考文献中间体

合成目标

【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