Schönenberger, Helmut and Brinkman, R. and Bamann, E. (1963) Resolution of N-(DL-N,N-dimethylalanyl)-L-y-ephedrine into its stereoisomeric forms of Craig partition. The possibility of resolution of racemic amino acids into optical isomers using countercurrent methods. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 296, pp. 33-37.
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DL-N,N-Dimethylalanine (I) was converted into N-(DL-N,N-dimethylalanyl)-L-y-ephedrine (II). II was resolved into its diastereoisomers by a Craig countercurrent partition process using 45:5:50 0.1M citrate buffer (pH 5.98)-MeOHCHCl3. N-(L-N,N-Dimethylalanyl)-L-y-ephedrine (III) m. 97-9 Deg, [alpha ]20D 70 Deg (c 0.007, 5N HCl), and N-(D-N,N-dimethylalanyl)-L-y-ephedrine m. 83-5 Deg, [alpha ]20D 100.2 Deg (c 0.023, 5N HCl). I (7.5 g.) was suspended in 100 ml. anhyd. tetrahydrofuran contg. 7 g. Et3N, 9 g. ClCO2Et slowly added, the mixt. stirred 5 hrs. below 0 Deg, 11 of L-(+)-y-ephedrine added, and stirring continued for 2 hrs. to give 7 g. II, b0.05 112 Deg. L-threo-3,4-Dimethyl-5-phenyloxazolidine, b12 108 Deg, was obtained as a by-product. The same procedure applied to L-N,N-dimethylalanine gave III.
|Additional information (public):||CAN 62:3222 41 Alkaloids 1568-05-4; 1877-43-6; 2246-11-9; 2673-88-3; 3205-45-6; 3406-37-9 (Derived from data in the 7th Collective Formula Index (1962-1966); 123618-06-4P Role: SPN (Synthetic preparation), PRP (Properties), PREP (Preparation) (Resolution of N-(DL-N,N-dimethylalanyl)-L-y-ephedrine into its stereoisomeric forms of Craig partition. The possibility of resolution of racemic amino acids into optical isomers using countercurrent methods); 2480-18-4 (Propionamide, 2-(dimethylamino)-N-(beta -hydroxy-alpha -methylphenethyl)-N-methyl-) (resolution of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Resolution (of amino acids, by countercurrent partition) Amino acids (resolution of, by countercurrent partition)|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 09:36|
|Last Modified:||19 Nov 2010 09:36|