(Z)-β-Fluoromethylene-m-tyrosine: synthesis, crystal structure and fluorination

Article abstract of DOI:10.1016/0022-1139(95)03267-H

(Z)-β-Fluoromethylene-m-tyrosine (2) has been prepared by acid hydrolysis of ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate (1) and its structure established by single crystal X-ray diffraction analysis.Fluorination of the amino acid 2 with acetyl hypofluorite yielded a mixture of products containing fluorine substituted on the ring (3a-c) as well as added across the vinylic double bond (4a,b).The mechanism for the formation of the diastereomeric adducts 4a and 4b is discussed based on tight ion pair intermediates.All major products of fluorination of 2 were isolated by semipreparative HPLC and their structures determined by spectral analyses. - Keywords: Mechanism-based inhibition; Fluoromethylene amino acid; Monoamine oxidase; Fluorination; Crystal structure