Separation of organic bases by Craig partition. VI. Correlations between the configuration and the phase distribution behavior of aminoacylephedrines

Abstract

cf. CA 62, 7857h. A series of diastereomeric aminoacylephedrine compds. were sepd. in a Craig phase distribution process in a mixt. of CHCl3, MeOH, and citrate buffer soln. (vol. 10:1:9) at 20 Deg (distribution coeff., K, and sepn. factor, beta = K2/KD, given): (L-N-dimethylphenylalanyl)-L-amphetamine, 1.1, (D-N-dimethylphenylalanyl)-L-amphetamine, 0.75, 1.4; N-(L-N-dimethylphenylalanyl)-L-norephedrine, 2.5, -; (N-(L-N-dimethylphenylalanyl)-D-norephedrine, 0.7, 3.5; N-(L-N-dimethylphenylalanyl)-L-nor-y-ephedrine, 1.2, -; N-(D-N-dimethylphenylalanyl)-L-nor-y-ephedrine, 0.35, 3.4; (L-N-dimethylphenylalanyl)-L-pervitine, 4.3, -; (D-N-dimethylphenylalanyl)-L-pervitine, 4.8, 1.1; N-(D-N-dimethylphenylalanyl)-L-ephedrine, 4.0, -; N-(D-N-dimethylphenylalanyl)-L-ephedrine, 0.87, 3.1; N-(D-N-dimethylphenylalanyl)-L-y-ephedrine, 7.2, -; N-(D-N-dimethylphenylalanyl)-L-y-ephedrine, 0.95, 7.9; N-(L-N-dimethylphenylalanyl)-D-erythro-diphenylethanolamine, 0.62, -; N-(D-N-dimethylphenylalanyl)-D-erythro-diphenylethanolamine, 0.58, 1.07; N-(L-N-dimethylalanyl)-D-threo-diphenylethanolamine, 0.61, -; N-(L-N-dimethylalanyl)-L-threo-diphenylethanolamine, 0.52, 1.17; N-(L-N-dimethylphenylalanyl)-D-erythro-diphenylethanolamine, 1.4, -; N-(D-N-dimethylphenylalanyl)-D-erythro-diphenylethanolamine, 0.35, 4.0; N-(L-N-dimethylphenylalanyl)-D-threo-diphenylethanolamine, 0.9, -; N-(D-N-dimethylphenylalanyl)-D-threo-diphenylethanolamine, 0.51, 1.75. The varying behavior of these compds. is based on interactions between the amide group and the OH group which are exposed to different configurational effects at the three asym. centers of the mol.