Biological Activity
m-Fluoro-DL-phenylalanine, a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine with potential use in antiviral and antimicrobial drug development.
Synthesis
General procedure for the synthesis of 3-fluoro-DL-phenylalanine from compound (CAS: 380-70-1): intermediate 231 (7.50 g, 21.43 mmol) was added to 94% hydrochloric acid (80 mL). The reaction mixture was stirred under reflux conditions for 15 h. The completion of the reaction was confirmed by TLC analysis. After completion of the reaction, the mixture was filtered to give white solid 233 in 86% yield. High resolution mass spectrometry (HRMS, ESI) analysis resulted in a calculated value of 184.0715 (M + H)+ for m/z, C9H10NO2 and a measured value of 184.0767.
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
[3] Organic Letters, 2018, vol. 20, # 19, p. 6298 - 6301
![Propanedioic acid, 2-(acetylamino)-2-[(3-fluorophenyl)methyl]-, 1,3-diethyl ester](/CAS/20210305/GIF/380-70-1.gif)
