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【结 构 式】

【分子编号】64395

【品名】N-{[3-(3,4,5-trifluorophenyl)-4,5-dihydro-5-isoxazolyl]methyl}acetamide

【CA登记号】

【 分 子 式 】C12H11F3N2O2

【 分 子 量 】272.2268296

【元素组成】C 52.95% H 4.07% F 20.94% N 10.29% O 11.75%

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)

3,4,5-Trifluorobenzaldehyde (I) is converted into oxime (II) upon treatment with hydroxylamine in aqueous EtOH. Subsequent oxidation of oxime (II) with N-chlorosuccimide produces the hydroximinoyl chloride (III). In situ conversion of (III) to the corresponding nitrile oxide, followed by cycloaddition with N-allyl acetamide (IV) generates the racemic isoxazoline (V). After resolution of (V) by means of chiral HPLC, displacement of the para-fluoride group with piperazine in hot DMSO furnishes (VI). Acylation of piperazine (VI) by means of acetoxyacetyl chloride (VII) gives rise to amide (VIII). Finally, methanolysis of the acetoxy group of (VIII) in the presence of K2CO3 leads to the target hydroxyacetylpiperazine derivative. (1,2)

1 Identification of phenylisoxazolines as novel and viable antibacterial agents active against Gram-positive pathogens. J Med Chem 2003, 46, 2, 284.
2 Thomas, R.C.; Barbachyn, M.R.; Morris, J.; Wishka, D.G.; Cleek, G.J. (Pfizer Inc.); Substd. aminophenyl isoxazoline derivs. useful as antimicrobials. JP 2002503655; US 6069141; WO 9941244 .
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) 64391 3,4,5-trifluorobenzaldehyde C7H3F3O 详情 详情
(II) 64392 3,4,5-trifluorobenzaldehyde oxime C7H4F3NO 详情 详情
(III) 64393 3,4,5-trifluoro-N-hydroxybenzenecarboximidoyl chloride C7H3ClF3NO 详情 详情
(IV) 64394 N-(2-propenyl)acetamide C5H9NO 详情 详情
(V) 64395 N-{[3-(3,4,5-trifluorophenyl)-4,5-dihydro-5-isoxazolyl]methyl}acetamide C12H11F3N2O2 详情 详情
(VI) 64396 N-({3-[3,5-difluoro-4-(1-piperazinyl)phenyl]-4,5-dihydro-5-isoxazolyl}methyl)acetamide C16H20F2N4O2 详情 详情
(VII) 10456 Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate 13831-31-7 C4H5ClO3 详情 详情
(VIII) 64397 2-[4-(4-{5-[(acetylamino)methyl]-4,5-dihydro-3-isoxazolyl}-2,6-difluorophenyl)-1-piperazinyl]-2-oxoethyl acetate C20H24F2N4O5 详情 详情
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