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【结 构 式】

【分子编号】38624

【品名】6-bromo-2-(bromomethyl)-9H-fluoren-9-one

【CA登记号】

【 分 子 式 】C14H8Br2O

【 分 子 量 】352.02492

【元素组成】C 47.77% H 2.29% Br 45.4% O 4.54%

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:(II)

The bromination of 6-bromo-2-methylfluoren-9-one (I) with NBS and AIBN in refluxing CCl4 gives the 2-bromomethyl compound (II), which is treated with potassium acetate in DMF to afford the acetoxymethyl derivative (III). The hydrolysis of (III) with NaOMe in methanol provides the hydroxymethyl compound (IV), which is treated with hexamethyldistannane and Pd(PPh3)4 in refluxing toluene to give the trimethylstannyl derivative (V). The condensation of (V) with the carbapenem triflate (VI) by means of a Pd catalyst in THF yields the adduct (VII), which is condensed with 1-methylimidazole by means of Tf2O in dichloromethane affording the imidazolium derivative (IX). The desilylation of (IX) with TBAF in THF gives the 1-hydroxyethyl derivative (X), which is finally treated with H2 over Pd/C in THF/ethanol/water to obtain the target compound as an inner salt. The intermediate carbapenem triflate (VI) has been obtained by reaction of 2-oxocarbapenam (XI) with Tf2O, followed by silylation with Tes-OTf.

1 Greenlee, M.L.; Dininno, F.P.; Cama, L.D.; Heck, J.V. (Merck & Co., Inc.); 2-(9-Fluorenonyl)-carbapenem antibacterial agents. EP 0472306; JP 1993105679; US 5034384 .
2 Greenlee, M.L.; Dininno, F.P.; Cama, L.D.; Heck, J.V. (Merck & Co., Inc.); 2-(9-Fluorenonyl)-carbapenem intermediates. US 5356889 .
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) 38623 6-bromo-2-methyl-9H-fluoren-9-one C14H9BrO 详情 详情
(II) 38624 6-bromo-2-(bromomethyl)-9H-fluoren-9-one C14H8Br2O 详情 详情
(III) 38625 (6-bromo-9-oxo-9H-fluoren-2-yl)methyl acetate C16H11BrO3 详情 详情
(IV) 38626 6-bromo-2-(hydroxymethyl)-9H-fluoren-9-one C14H9BrO2 详情 详情
(V) 38627 2-(hydroxymethyl)-6-(trimethylstannyl)-9H-fluoren-9-one C17H18O2Sn 详情 详情
(VI) 38628 4-nitrobenzyl (5R,6S)-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-3-[[(trifluoromethyl)sulfonyl]oxy]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C23H29F3N2O9SSi 详情 详情
(VII) 38629 4-nitrobenzyl (5R,6S)-3-[7-(hydroxymethyl)-9-oxo-9H-fluoren-3-yl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C36H38N2O8Si 详情 详情
(VIII) 38630 1-methyl-1H-imidazole 616-47-7 C4H6N2 详情 详情
(IX) 38631 1-methyl-3-[[6-((5R,6S)-2-[[(4-nitrobenzyl)oxy]carbonyl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-3-yl)-9-oxo-9H-fluoren-2-yl]methyl]-1H-imidazol-3-ium chloride C40H43ClN4O7Si 详情 详情
(X) 38632 3-[[6-((5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[[(4-nitrobenzyl)oxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)-9-oxo-9H-fluoren-2-yl]methyl]-1-methyl-1H-imidazol-3-ium chloride C34H29ClN4O7 详情 详情
(XI) 22686 4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C16H16N2O7 详情 详情
Extended Information