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【结 构 式】

【分子编号】45470

【品名】ethyl 2-oxo-2-[(2-phenylacetyl)peroxy]acetate

【CA登记号】

【 分 子 式 】C12H12O6

【 分 子 量 】252.22368

【元素组成】C 57.14% H 4.8% O 38.06%

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:(IV)

Treatment of phenylacetyl chloride (I) with tris(trimethylsilyloxy)ethylene (A) in the presence of SnCl4 affords 1-hydroxy-3-phenylpropan-2-one (II), which is then condensed with ethyl oxalyl chloride (III) in THF in the presence of Et3N to yield (IV). Phenylhexanoate derivative (IV) is cyclized by means of DBU in DMF to provide valerolactone derivative (V), which is then condensed with 1-methylindole-3-carboxaldehyde (VI) in HOAc to furnish derivative (VII). Finally, the target compound is obtained by treatment of (VII) with NaOMe in MeOH.

1 Liu, K.; Szalkowski, D.; Xu, L.; et al.; Discovery of a potent, highly selective, and orally efficacious small-molecule activator of the insulin receptor. J Med Chem 2000, 43, 19, 3487.
2 Wood, H.B.; Jones, A.B.; Zhang, B.; Liu, K. (Merck & Co., Inc.); Antidiabetic agents. EP 1067925; US 6077849; WO 9951225 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 14534 2,2,7,7-tetramethyl-4-[(trimethylsilyl)oxy]-3,6-dioxa-2,7-disila-4-octene; 1,2-bis[(trimethylsilyl)oxy]vinyl trimethylsilyl ether; TRIS(TRIMETHYLSILYLOXY)ETHYLENE 69097-20-7 C11H28O3Si3 详情 详情
(I) 25890 2-phenylacetyl chloride;Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride 103-80-0 C8H7ClO 详情 详情
(II) 45469 2-phenylethaneperoxoic acid C8H8O3 详情 详情
(III) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(IV) 45470 ethyl 2-oxo-2-[(2-phenylacetyl)peroxy]acetate C12H12O6 详情 详情
(V) 45471 3-hydroxy-4-phenyl-2H-pyran-2,5(6H)-dione C11H8O4 详情 详情
(VI) 45472 1-Methylindole-3-carboxaldehyde; 1-Methyl-1H-indole-3-carbaldehyde; 1-Methylindole-3-carbaldehyde 19012-03-4 C10H9NO 详情 详情
(VII) 45473 3-hydroxy-6-[(Z)-(3-methyl-3H-benzimidazol-1-yl)methylidene]-4-phenyl-2H-pyran-2,5-dione 455-15-2 C20H16N2O4 详情 详情
Extended Information