A series of 25 compounds were synthesized based on structure modification of the model methyl 3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropanoateas potent HDACIs. Saponification and hydrazinolysis of the model ester afforded the corresponding acid and hydrazide, respectively.The model ester was transformed into corresponding trichloroacetimidate or acetate by the reaction with trichloroacetonitrile and acetic anhydride, respectively. N-alkyl-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropan-amides and methyl 2-[(3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropanoyl)amino] alkanoates were obtained by the reaction ofcorresponding acid or hydrazide with amines and amino acid esters via DCC and azidecoupling methods. Methyl 3-aryl-3-(4-chlorophenyl)-2,2-dimethylpropanoates were obtainedin good yields and short reaction timefrom the corresponding trichloroacetimidate or acetate by the reaction with C-active nucleophiles in the presence of TMSOTf (0.1 eq %) via C-C bond formation.
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Convenient synthesis of some new 3-(4-chloro-phenyl)-3-hydroxy-2,2-dimethyl-propionic acid methyl ester derivatives of expected Anticancer Activity
Published: 14 November 2019 by MDPI in The 23rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: carboxamides, Amino acids, DCC coupling, azide coupling, C-nucleophiles trichloroacetimidate coupling, acetate coupling.