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[摘要]:Two routes for the synthesis of N-ethyl-N-(4-nitrophenylsulfonyl)-alpha,beta-dehydroamino acid derivatives from serine, threonine and phenylserine derivatives are presented. One route consists of dehydration of N-(4-nitrophenylsulfonyl)-beta-hydroxyamino acid esters with di-tert-butyl dicarbonate catalyzed by 4-(dimethylamino)pyridine, followed by alkylation of the N-(4-nitrophenylsulfonyl)-alpha,beta-dehydroamino acid methyl esters obtained with triethyloxonium tetrafluoroborate. The second strategy applied the same procedures but in inverse order: alkylation followed by dehydration. These methods made it possible to obtain for the first time, new non-natural amino acids, which incorporate both an N-ethyl and an alpha,beta-dehydro moiety. |
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