Schönenberger, Helmut and Brinkmann, R. and Bamann, E. (1964) Separation of organic bases by Craig partition. V. Synthesis and separation of aminoacylephedrine isomers, a new class of local anesthetics. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 297 (12), pp. 721-727.
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cf. CA 61, 2737g. N, N-Dimethylalanine (I) and N,N-dimethylphenylalanine (II) were condensed by the mixed anhydride method with amphetamine (III), ephedrine (IV), and y-ephedrine (V) to give RCH2CH(NMe2)CONR1-CHMeCHPhR2 (VI) (R = H or Ph, R1 = H or Me, R2 = H or OH). By Craig partition in CHCl3-MeOH-aq. buffer systems, individual isomers were sepd. from the diastereoisomeric mixts. obtained from DL-I or II [amino acid, base, m.p., [alpha ]20D (5N HCl), and % yield VI given]: L-I, L-V, 97-9 Deg, 70 Deg, 34; D-I, L-V, 83-5 Deg, 100 Deg, 42; L-II, L-IV, 120 Deg, -48 Deg, 37; D-II, L-IV, 125 Deg, -75 Deg, 26; D-II, D-IV, 118-20 Deg, 48 Deg, 48; L-II, D-IV, 125 Deg, 73 Deg, 26; L-II, L-V, 128 Deg, 68 Deg, 18; D-II, L-V, 114 Deg, -32 Deg, 36; D-II, D-V, 128 Deg, -68 Deg, 19; L-II, D-V, 114 Deg, 32 Deg, 46. Compds. that could not be readily sepd. from the diastereoisomeric mixts. were prepd. with optically active amino acids (same data given): L-I, L-III, - (b0.05 73 Deg), -, 55; D-I, L-III, - (b0.1 135 Deg), -, 42; L-I, L-IV, 87-8 Deg, -46 Deg, 66; D-I, L-IV, -, -19 Deg, 45; L-II, L-III, 64-6 Deg, 57 Deg, 48; D-II, L-III, 88-9 Deg, -46 Deg 62.
|Additional information (public):||CAN 62:44195 44 Amino Acids, Peptides, and Proteins 2076-49-5; 2480-19-5; 2480-23-1; 2480-26-4; 2566-35-0; 3913-67-5; 25271-29-8 (Derived from data in the 7th Collective Formula Index (1962-1966); 300-62-9 (Phenethylamine, alpha -methyl-) (aminoacyl derivs., isomers of); 299-42-3 (Ephedrine) (aminoacyl, isomers of); 2480-17-3P (Propionamide, 2-(dimethylamino)-N-(alpha -methylphenethyl)-, stereoisomers); 2480-18-4P (Propionamide, 2-(dimethylamino)-N-(beta -hydroxy-alpha -methylphenethyl)-N-methyl-, stereoisomers); 2480-21-9P (Hydrocinnamamide, alpha -(dimethylamino)-N-(beta -hydroxy-alpha -methylphenethyl)-N-methyl-, hydrochloride, stereoisomers); 10385-91-8P (Hydrocinnamamide, alpha -(dimethylamino)-N-(beta -hydroxy-alpha -methylphenethyl)-N-methyl-, stereoisomers); 802005-41-0P (Hydrocinnamamide, alpha -(dimethylamino)-N-(alpha -methylphenethyl)-, stereoisomers) Role: PREP (Preparation) (prepn. of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Partition (of aminoacyl ephedrines between aq. solns. and org. solvents)|
|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 09:32|
|Last Modified:||19 Nov 2010 09:32|