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【结 构 式】

【分子编号】64197

【品名】ethyl 2-[2-[(tert-butoxycarbonyl)amino]-4-(trifluoromethyl)phenyl]-2-oxoacetate

【CA登记号】

【 分 子 式 】C16H18F3NO5

【 分 子 量 】361.3178696

【元素组成】C 53.19% H 5.02% F 15.77% N 3.88% O 22.14%

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)

The reaction of 3-(trifluoromethyl)aniline (I) with Boc2O gives the carbamate (II), which is condensed with 14C labeled diethyl oxalate (III) by means of BuLi to yield the ketoester (IV). The cyclization of (IV) by means of refluxing aq. HCl affords the labeled 6-(trifluoromethyl)isatin (V), which is condensed with 5-chloro-2-methoxyphenylmagnesium bromide (VI) to provide the hydroxyketone (VII). The fluorination of (VII) with DAST gives the target compound as a racemic mixture (VIII), which is finally submitted to optical resolution by chiral HPLC.

1 Dischino, D.D.; Gribkoff, V.K.; Hewawasam, P.; Luke, G.M.; Rinehart, J.K.; Spears, T.L.; Starrett, J.E. Jr.; Synthesis of 3H and 14C labeled (S)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-indol-2-one, MaxiPost(TM). An agent for post-stroke neuroprotection. J Label Compd Radiopharm 2003, 46, 2, 139.
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) 26347 3-(trifluoromethyl)phenylamine; 3-(trifluoromethyl)aniline; 3-aminobenzotrifluoride 98-16-8 C7H6F3N 详情 详情
(II) 39335 tert-butyl 3-(trifluoromethyl)phenylcarbamate C12H14F3NO2 详情 详情
(III) 17571 Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate 95-92-1 C6H10O4 详情 详情
(III) 64193 allyl (2R,3S,4R,5R)-2-[({(2R,3R,4R,5S,6R)-5-{[bis(allyloxy)phosphoryl]oxy}-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(Z)-11-octadecenoylamino]tetrahydro-2H-pyran-2-yl}oxy)methyl]-6-{[tert-butyl(dimethyl)silyl]oxy}-4-(decyloxy)-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-3-yl carbonate C82H151N2O18PSi 详情 详情
(IV) 39336 ethyl 2-[2-[(tert-butoxycarbonyl)amino]-4-(trifluoromethyl)phenyl]-2-oxoacetate C16H18F3NO5 详情 详情
(IV) 64197 ethyl 2-[2-[(tert-butoxycarbonyl)amino]-4-(trifluoromethyl)phenyl]-2-oxoacetate C16H18F3NO5 详情 详情
(V) 39337 6-(trifluoromethyl)-1H-indole-2,3-dione C9H4F3NO2 详情 详情
(V) 64198 6-(trifluoromethyl)-1H-indole-2,3-dione C9H4F3NO2 详情 详情
(VI) 39338 bromo(5-chloro-2-methoxyphenyl)magnesium C7H6BrClMgO 详情 详情
(VII) 39339 3-(5-chloro-2-methoxyphenyl)-3-hydroxy-6-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one C16H11ClF3NO3 详情 详情
(VII) 64199 3-(5-chloro-2-methoxyphenyl)-3-hydroxy-6-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one C16H11ClF3NO3 详情 详情
(VIII) 43889 3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one C16H10ClF4NO2 详情 详情
(VIII) 64200 3-(5-Chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-indol-2-one C16H10ClF4NO2 详情 详情
Extended Information