Reaction Steps
Condensation of N-tert-butoxycarbonyl-L-inethionine (1a) with 2-aminopyridine (2j) according to General Procedure A, resulted, after purification on a SILICA GEL column (hexane-acetone 3:1), in (3o) (C15H23N3O3S1, 62%), Rf=0.33 (hexane-acetone 3:1), m.p. 135°-137° C., [α]D23 =-28.2° (c 0.11, CHCl3), IR (KBr) ν: 432, 459, 471, 496, 527, 623, 681, 737, 775, 829, 847, 864, 924, 964, 999, 1028, 1053, 1099, 1165, 1252, 1283, 1304, 1366, 1389, 1435, 1462, 1532, 1580, 1603, 1674, 1711, 2363, 2832, 2915, 2953, 2974, 2999, 3046, 3127, 3262 cm-1, 1H NMR (CDCl3) δ: 8.647-8.655 (br s, 1H, Ar--NH), 8.264-8.290 (m, 1H, ArH), 8.1705 (d, 1H, J 8.1 Hz, ArH), 7.659-7.718 (m, 1H, ArH), 7.016-7.055 (m, 1H, ArH), 5.210-5.227 (m, 1H, NH), 4.440 (m, 1H, Hα), 2.540-2.638 (m, 2H, CH2γ), 2.138-2.253 (m, 1H, Hβ), 2.099 (s, 3H, CH3ε), 1.968-2.040 (m, 1H, Hβ), 1.436 (s, 9H, t-Bu); EIMS (70 eV) m/z (%): 325 (M+, 5).
