Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic acid.
Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidene)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine-3-carboxylic acid, a new fluorinated heterocyclic amino acid.
Van Hende
Eva
E
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Verniest
Guido
G
Deroose
Frederik
F
Thuring
Jan-Willem
JW
Macdonald
Gregor
G
De Kimpe
Norbert
N
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001385:Azetines / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C551692:1-Boc-3-fluoroazetidine-3-carboxylic acid; D000596:Amino Acids; D001385:Azetines; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds