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【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

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