New N,N'-bis:alkyl -carbamyl undecyl adipamide cpds. - used as chiral phase for gas chromatography for high sepn. factor

摘要

New chiral stationary phases for gas chromatography consist of an N,N'-bis 1-(alkylcarbamyl) -alkyl)-dicarbamide of formula R1-NH-CO-(CH2)m-CO-NH-R1 (I); where R1 = CH3=(CH2)n-CH-CO-NH-R2; R2 = t-butyl, S(1)phenylethyl, neopentyl or adamantoyl; m = 0-10; n = 9-15. New N,N'-bis (1-(alkylcarbamoyl) -n-undecyl)-adipamides (IA) are of formula (I) with m = 4 and n = 9. (I) are prepd. (claimed) by (a) brominating the long-chain fatty acid in the 2-position; (b) converting the resultant 2-bromo fatty acid bromide to the alpha-bromomethyl ester with MeOH and ammonolysis to the amide with NH3 in MeOH; (c) sepg. this into the optical antipodes with crude acylase from pigs' kidneys; (d) protecting the N-terminal of the free (S)-2-aminocarboxylic acid with protective gps. for further peptide chemical coupling; (e) amidation with the specified substits. by the usual peptide chemical methods; (f) acylation with acid chlorides or other reagents used in peptide chemistry, after removing the protective gps.; (g) pre-purificn. by normal methods; and (h) fine purificn. by chromatography. USE/ADVANTAGE - (I) are useful for capillary gas chromatography for enantiomer analysis of aminoacid derivs. and aminoacid analysis by enantiomer labelling. High sepn. factors are obtd. by using long-chain optically active 2-aminocarboxylic acids and modification of the acyl and amido gps. makes them temp.-stable. The distance between the chiral centres can be selected at will and the m.pt. and hence properties of the chiral phase can also be modifie