ethyl 2-(hydroxyimino)-2-(4-phenoxyphenyl)acetate -Drug Synthesis Database

【结构式】

【分子编号】60080

【品名】ethyl 2-(hydroxyimino)-2-(4-phenoxyphenyl)acetate

【CA登记号】

【分子式】C₁₆H₁₅NO₄

【分子量】285.29944

【元素组成】C 67.36% H 5.3% N 4.91% O 22.43%

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：(VII)

Friedel-Crafts acylation of diphenyl ether (IV) with ethyl chloroglyoxylate (V) affords the (4-phenoxyphenyl)glyoxylate (VI). This is then treated with hydroxylamine to produce a mixture of Z- and E-oximes (VII) and (VIII), which can be separated by recrystallization, followed by column chromatography. The desired Z-oxime (VII) is alkylated by the benzyl chloride derivative (III) to furnish the O-benzyl oxime (IX). Finally, saponification of the ethyl ester group of (IX) with NaOH in MeOH gives rise to the target carboxylic acid

参考文献中间体

合成目标

【1】 Imoto, H.; Imamiya, E.; Momose, Y.; Sugiyama, Y.; Kimura, H.; Sohda, T.; Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives. Chem Pharm Bull 2002, 50, 10, 1349.
【2】 Kimura, H.; Momose, Y.; Odaka, H.; Sakamoto, J.; Imoto, H. (Takeda Chemical Industries, Ltd.); Oxyiminoalkanoic acid derivs. with hypoglycemic and hypolipidemic activity. EP 1077957; JP 2000034266; JP 2000198772; US 6251926; US 6495581; WO 9958510 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	60074	4-(chloromethyl)phenyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl ether; 4-{[4-(chloromethyl)phenoxy]methyl}-5-methyl-2-phenyl-1,3-oxazole		C₁₈H₁₆ClNO₂	详情	详情
(IV)	60075	1-phenoxybenzene; diphenyl ether		C₁₂H₁₀O	详情	详情
(V)	11043	Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride	4755-77-5	C₄H₅ClO₃	详情	详情
(VI)	60076	ethyl 2-oxo-2-(4-phenoxyphenyl)acetate		C₁₆H₁₄O₄	详情	详情
(VII)	60080	ethyl 2-(hydroxyimino)-2-(4-phenoxyphenyl)acetate		C₁₆H₁₅NO₄	详情	详情
(VIII)	60077	ethyl 2-(hydroxyimino)-2-(4-phenoxyphenyl)acetate		C₁₆H₁₅NO₄	详情	详情
(IX)	60078	ethyl 2-[({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)imino]-2-(4-phenoxyphenyl)acetate		C₃₄H₃₀N₂O₆	详情	详情

Extended Information