Advances in the stereoselective synthesis of antifungal agents and ...

Chapter 8 189(R,S)-(±)-1-(2-Octyl)imidazole-4,5-dicarboxylic acid (±)-34a.Synthetic method 7.8.1Recrystallized from EtOH.1H NMR (200 MHz, CDCl 3 ) δ = 0.86 (t, J = 6.0 Hz, 3H), 1.28 (m,8H), 1.70 (d, J = 6.0 Hz, 3H), 1.90 (m, 2H), 5.93 (m, 1H), 8.68 (s,1H).IR (CHCl 3 ): ν cm-1= 1735 cm -1M.P. = 188-190 °C.Elementary Analysis. calcd. for C 13 H 20 N 2 0 4 : C, 58.19; H, 7.51; N,10.44. Found: C, 58.31; H, 7.58; N, 10.29.(S)-(+)-1-(2-Octyl)imidazole-4,5-dicarboxylic acid (S)-(+)-34a.Synthetic method 7.8.1[α] 20 D +20.0 (c 0.95, CHCl 3 ).Physical and spectral data were identical with those described abovefor the racemate (±)-34a.(R,S)-(±)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarboxylic acid (±)-34b.Synthetic method 7.8.1Recrystallized from EtOH,1H NMR (200 MHz, DMSO-d 6 ) δ= 1.51 (d, J = 6.9 Hz, 3H), 3.10(dd, J = 13.1, 6.7 Hz, 1H), 3.25 (dd, J = 13.1, 6.7 Hz, 1H), 6.07(sextet, J = 6.9 Hz, 1H), 7.23 (m, 5H), 9.36 (s, 1H).IR (nujol mull) ν cm-1=1735M.P.= 210-212 °C.Elementary Analysis. calcd. for C 14 H 14 N 2 0 4 : C, 61.30; H, 5.14; N,10.22. Found: C, 61.44; H, 5.27; N, 9.98.(S)-(+)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarboxylicacid (S)-(+)-34b.Synthetic method 7.8.1[α] 20 D +2.0 (c 1.40, C 6 H 5 N).Physical and spectral data were identical with those described abovefor the racemate (±)-34b.(R,S)-(±)-1-(1-Phenyl-1-propyl)imidazole-4,5-dicarboxylic acid (±)-34c.Synthetic method 7.8.1