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1.发明授权PROCESS FOR THE SYNTHESIS OF N-(4-CYANO-3-TRIFLUOROMETHYLPHENYL)-3-(4-FLUOROPHENYLSULPHONYL)-2-HYDROXY-2-METHYLPROPIONAMIDE 有权PROCESS FOR N-（4-氰基-3-三氟甲基苯基）-3-（4- FLUROPHENYLSULFONYL）-2-羟基-2-甲基丙酰胺的制备
公开(公告)号：EP1189898B1
公开(公告)日：2003-03-12
申请号：EP00937111.3
申请日：2000-05-26
发明人： SÖRÖS, Béla , TUBA, Zoltán , GALIK, György; , BOR, Adám; , DEMETER, Adám , TRISCHLER, Ferenc; , HORVATH, János , BRLIK, János
IPC分类号： C07D327/10 , C07C253/30 , C07C303/28 , C07C309/66 , C07C319/14 , C07C323/60 , C07C315/02 , C07C317/46
CPC分类号： C07C253/30 , C07C303/28 , C07C315/02 , C07C319/14 , C07D327/10 , C07C317/46 , C07C255/60 , C07C309/66 , C07C323/60
摘要： Racemic or optically pure N-(4-cyano-3-trifluoromethylphenyl)-3-(4 -fluorophenylsulphonyl)-2-hydroxy-2-methylpropionamide of formula (I) is prepared by the following process: 2,3-dihydroxy-2-methylpropionic acid of formula (VII) is reacted with thionyl chloride to form 4-chlorocarbonyl-4-methyl-1,3,2-dioxathiolane-2-one of formula (VI), which is reacted with 4-cyano-3-trifluoromethylaniline. The resulting 4-{[4-cyano-3-(trifluoromethyl)anilino]carbonyl}-4-methyl-1,3,2-dioxathiolane-2-one of formula (V) is hydrolysed to form N-[4-cyano-3-(trilfuoromethyl)phenyl]-2,3-dihydroxy-2-methylpropionamide of formula (IV), which is sulfonylated with a sulfonyl halogenide of formula R-SO2-X, in a halogenated hydrocarbon solvent in the presence of a tertiary amine base. The sulphonic ester derivative of formula (III) obtained is reacted with 4-fluorothiophenol in the presence of a base to give a thioether of formula (II) which is oxidized using an inorganic peroxy compound or aqueous hydrogen peroxide.
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2.发明公开PROCESS FOR THE SYNTHESIS OF N-(4-CYANO-3-TRIFLUOROMETHYLPHENYL)-3-(4-FLUOROPHENYLSULPHONYL)-2-HYDROXY-2-METHYLPROPIONAMIDE 有权PROCESS FOR N-（4-氰基-3-三氟甲基苯基）-3-（4- FLUROPHENYLSULFONYL）-2-羟基-2-甲基丙酰胺的制备
公开(公告)号：EP1189898A1
公开(公告)日：2002-03-27
申请号：EP00937111.3
申请日：2000-05-26
发明人： SÖRÖS, Béla , TUBA, Zoltán , GALIK, György; , BOR, Adám; , DEMETER, Adám , TRISCHLER, Ferenc; , HORVATH, János , BRLIK, János
IPC分类号： C07D327/10 , C07C253/30 , C07C303/28 , C07C309/66 , C07C319/14 , C07C323/60 , C07C315/02 , C07C317/46
CPC分类号： C07C253/30 , C07C303/28 , C07C315/02 , C07C319/14 , C07D327/10 , C07C317/46 , C07C255/60 , C07C309/66 , C07C323/60
摘要： Racemic or optically pure N-(4-cyano-3-trifluoromethylphenyl)-3-(4 -fluorophenylsulphonyl)-2-hydroxy-2-methylpropionamide of formula (I) is prepared by the following process: 2,3-dihydroxy-2-methylpropionic acid of formula (VII) is reacted with thionyl chloride to form 4-chlorocarbonyl-4-methyl-1,3,2-dioxathiolane-2-one of formula (VI), which is reacted with 4-cyano-3-trifluoromethylaniline. The resulting 4-{[4-cyano-3-(trifluoromethyl)anilino]carbonyl}-4-methyl-1,3,2-dioxathiolane-2-one of formula (V) is hydrolysed to form N-[4-cyano-3-(trilfuoromethyl)phenyl]-2,3-dihydroxy-2-methylpropionamide of formula (IV), which is sulfonylated with a sulfonyl halogenide of formula R-SO2-X, in a halogenated hydrocarbon solvent in the presence of a tertiary amine base. The sulphonic ester derivative of formula (III) obtained is reacted with 4-fluorothiophenol in the presence of a base to give a thioether of formula (II) which is oxidized using an inorganic peroxy compound or aqueous hydrogen peroxide.
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