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.