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【结 构 式】

【分子编号】62678

【品名】4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[7-(3-pyridinylcarbonyl)imidazo[5,1-b][1,3]thiazol-2-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C28H23N5O7S

【 分 子 量 】573.58612

【元素组成】C 58.63% H 4.04% N 12.21% O 19.53% S 5.59%

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:(VIII)

Metalation of 7-iodoimidazo[5,1-b]thiazole (I) with ethylmagnesium bromide, followed by addition to 3-pyridinecarboxaldehyde (II) provides carbinol (III), which is further oxidized to ketone (IV) by means of MnO2. Lithiation of (IV) and further treatment with chlorotributyltin affords the stannyl derivative (V). The carbapenem ketone (VI) is converted into the vinyl triflate (VII) upon treatment with trifluoromethanesulfonic anhydride and diisopropyl ethylamine. Then, Stille coupling between vinyl triflate (VII) and the stannyl derivative (V) gives rise to the imidazothiazolyl carbapenem (VIII). Quaternization of the pyridine ring of (VIII) with iodoacetamide furnishes the pyridinium salt (IX). Finally the p-nitrobenzyl ester group of (IX) is removed by hydrogenolysis over Pd/C to provide the title compound

1 Shitara, E.; Yamamoto, Y.; Kano, Y.; Maruyama, T.; Takahashi, M.; Atsumi, K.; CP5609, a novel parenteral carbapenem: Synthesis and structure-activity relationships. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-319.
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) 47193 7-iodoimidazo[5,1-b][1,3]thiazole C5H3IN2S 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 62675 imidazo[5,1-b][1,3]thiazol-7-yl(3-pyridinyl)methanol C11H9N3OS 详情 详情
(IV) 62676 imidazo[5,1-b][1,3]thiazol-7-yl(3-pyridinyl)methanone C11H7N3OS 详情 详情
(V) 62677 3-pyridinyl[2-(tributylstannyl)imidazo[5,1-b][1,3]thiazol-7-yl]methanone C23H33N3OSSn 详情 详情
(VI) 22575 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C17H18N2O7 详情 详情
(VII) 38750 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C18H17F3N2O9S 详情 详情
(VIII) 62678 4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[7-(3-pyridinylcarbonyl)imidazo[5,1-b][1,3]thiazol-2-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C28H23N5O7S 详情 详情
(IX) 62679 1-(2-amino-2-oxoethyl)-3-{[2-((4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-{[(4-nitrobenzyl)oxy]carbonyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)imidazo[5,1-b][1,3]thiazol-7-yl]carbonyl}pyridinium iodide C30H27IN6O8S 详情 详情
Extended Information