Substitution of halogen atom in α-halonitro compounds of the aliphatic series 6. Preparation and reduction of alkyl α-halo- and α-sulfosubstituted α-nitrocarboxylates

Article abstract of DOI:10.1007/BF00717345

Ethyl α-halo-α-nitropropionate and -butyrate were prepared by alkylating ammonium salts of ethyl bromo- and chloronitroacetates.The addition of alkyl acrylates to alkyl chloronitroacetates or their salts gives dialkyl α-chloro-α-nitroglutarates.Sodium salts of ethyl α-nitro-α-sulfo-β-hydroxypropionate and -butyrate were obtained by the sulfodehalogenation of ethyl α-chloro-α-nitro-β-hydroxypropionate and -butyrate with sodium dithionite.Esters of α-amino acid hydrochlorides were prepared by the reduction of alkyl α-chloro-α-nitrocarboxylates.The hydrogenation of alkyl nitrosulfoacetates leads to the corresponding disodium salts of alkyl aminodisulfoacetates and piperazine-2,5-dione. - Key words: halonitrocarboxylates, alkylation, Michael reaction, sulfodehalogenation, catalytic hydrogenation; amino acids; alkyl aminodisulfoacetates.