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【结 构 式】

【分子编号】30228

【品名】6-[((2R)-2-hydroxy-3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propyl)oxy]-3,4-dihydro-2(1H)-quinolinone

【CA登记号】

【 分 子 式 】C22H23N3O3S

【 分 子 量 】409.50904

【元素组成】C 64.53% H 5.66% N 10.26% O 11.72% S 7.83%

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:(VI)

The enantiomerically pure sulfoxide was prepared by a different route, starting from the alkylation of hydroxyquinolinone (A) with (S)-glycidyl tosylate (IV) to give the chiral epoxide (V). Ring opening with mercaptoimidazole (I) afforded the enantiomerically rich (R)-mercapto alcohol (VI), which after recrystallization from EtOH provided the pure (R)-isomer. Oxidation with m-chloroperbenzoic acid yielded a diastereomeric mixture of hydroxy sulfoxides (VII). After separation by column chromatography, the required (S)-sulfoxide was converted to mesylate (VIII), and finally reduced with lithium triethylborohydride to afford the target (S)-compound.

1 Nishi, T.; Chu, G.-N.; Okada, M.; Tamura, K.; Unemi, F.; Koga, Y.; Kido, M.; Igawa, T.; Ozeki, Y.; Uno, T.; Synthesis of 2(1H)-quinolinone derivatives and their inhibitory activity on the release of 12(S)-hydroxyeicosatetraenoic acid (12-HETE) from platelets. Chem Pharm Bull 1995, 43, 10, 1724.
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) 30226 6-Hydroxy-2-oxo-1,2,3,4-tetrahydroquinoline; 6-Hydroxy-3,4-dihydro-2(1H)-quinolinone; 6-Hydroxy-3,4-dihydrocarbostyril C9H9NO2 详情 详情
(I) 30223 1-(2-methylphenyl)-1H-imidazol-2-ylhydrosulfide; 1-(2-methylphenyl)-1H-imidazole-2-thiol C10H10N2S 详情 详情
(IV) 16740 (2S)-(+)-Glycidyl tosylate; (2S)oxiranylmethyl 4-methylbenzenesulfonate 70987-78-9 C10H12O4S 详情 详情
(V) 30227 6-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone C12H13NO3 详情 详情
(VI) 30228 6-[((2R)-2-hydroxy-3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propyl)oxy]-3,4-dihydro-2(1H)-quinolinone C22H23N3O3S 详情 详情
(VII) 30229 6-[((2R)-2-hydroxy-3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfinyl]propyl)oxy]-3,4-dihydro-2(1H)-quinolinone C22H23N3O4S 详情 详情
(VIII) 30230 (1R)-2-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfinyl]-1-[[(2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)oxy]methyl]ethyl methanesulfonate C23H25N3O6S2 详情 详情
Extended Information