Journal of Lipid Research, Vol 26, 258-262, Copyright © 1985 by Lipid Research, Inc.
Preparation of retinamides by use of retinoyl fluoride
AB Barua and JA Olson
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.