Preparation of retinamides by use of retinoyl fluoride.
Retinoyl fluoride (2) prepared from retinoic acid (1) by reaction with diethylaminosulfurtrifluoride is a stable crystalline compound not easily hydrolyzed by water. By reacting retinoyl fluoride with water-soluble amines in the presence of sodium bicarbonate, retinamide (4), N-retinoyl glycine (6), N-retinoyl DL-phenylalanine (7), alpha-N-retinoyl-L-lysine (11), N-retinoyl 4-aminophenol (4-hydroxyphenylretinamide) (8), and N-retinoyl-2-amino-2-deoxy-D-glucose (2-deoxy-D-glucose-2-retinamide) (9) have been prepared in good yields and characterized by UV absorption, 1H NMR, IR spectra, mass spectrometry, and elemental analysis.
D055598:Chemical Phenomena; D002621:Chemistry; D008722:Methods; D014212:Tretinoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D014212:Tretinoin; C038255:retinoyl fluoride