合成路线:This compound has been obtained by several related ways:1.The condensation of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (I) with rhodanine (II) by means of NaOAc in refluxing HOAc gives 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III),which is reduced with H2 over Pd/C in hot ethanol to yield the target compound along with its benzylidene analogue; these are separated by chromatography.2.The 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III) is reduced with 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester (IV) in hot toluene to give 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V),which is desulfurized to the target compound with H2 over 5% Pd/C (3) or with a great excess of Zn in acetic acid.3.The reaction of 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V) with ammonia and formaldehyde in methanol also gives the target compound through the nonisolated intermediate (VI).
参考文献标题:Cpds.for treating inflammatory bowel disease
文献作者:Gidda,J.S.; Panetta,J.A.; Phillips,M.L.(Eli Lilly and Company)
参考来源:EP 0434394; JP 1992279573; US 5216002
合成路线:This compound has been obtained by several related ways:1.The condensation of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (I) with rhodanine (II) by means of NaOAc in refluxing HOAc gives 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III),which is reduced with H2 over Pd/C in hot ethanol to yield the target compound along with its benzylidene analogue; these are separated by chromatography.2.The 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III) is reduced with 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester (IV) in hot toluene to give 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V),which is desulfurized to the target compound with H2 over 5% Pd/C (3) or with a great excess of Zn in acetic acid.3.The reaction of 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V) with ammonia and formaldehyde in methanol also gives the target compound through the nonisolated intermediate (VI).
参考文献标题:The development of a manufacturable synthesis of LY213829
文献作者:Slattery,B.J.; et al.
参考来源:Org Process Res Dev 2000,4(4),295
合成路线:This compound has been obtained by several related ways:1.The condensation of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (I) with rhodanine (II) by means of NaOAc in refluxing HOAc gives 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III),which is reduced with H2 over Pd/C in hot ethanol to yield the target compound along with its benzylidene analogue; these are separated by chromatography.2.The 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III) is reduced with 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester (IV) in hot toluene to give 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V),which is desulfurized to the target compound with H2 over 5% Pd/C (3) or with a great excess of Zn in acetic acid.3.The reaction of 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V) with ammonia and formaldehyde in methanol also gives the target compound through the nonisolated intermediate (VI).
参考文献标题:Synthesis of 4-Thiazolidinones from rhodanines by thiocarbonyl removal
文献作者:Hansen,M.M.; Harkness,A.R.
参考来源:Tetrahedron Lett 1994,35(38),6971
合成路线:This compound has been obtained by several related ways:1.The condensation of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (I) with rhodanine (II) by means of NaOAc in refluxing HOAc gives 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III),which is reduced with H2 over Pd/C in hot ethanol to yield the target compound along with its benzylidene analogue; these are separated by chromatography.2.The 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (III) is reduced with 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester (IV) in hot toluene to give 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V),which is desulfurized to the target compound with H2 over 5% Pd/C (3) or with a great excess of Zn in acetic acid.3.The reaction of 5-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-thioxothiazolidin-4-one (V) with ammonia and formaldehyde in methanol also gives the target compound through the nonisolated intermediate (VI).
参考文献标题:Kinetic resolution of a racemic sulfide by enantioselective sulfoxide formation
文献作者:Phillips,M.L.; Panetta,J.A.; Berry,D.M.
参考来源:J Org Chem 1992,57(14),4047
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