Acetic Acid → HCID 19388525, compound

Participants

Reaction Steps

R-(+)-prolinamide, 11, was converted to R-(+)-N-trilyl prolinamine, 12, using the procedure published in the literature (Hogberg, T., et al., Acta. Chem. Scand. 43, 660-664 (1989)), but using trityl bromide instead of trityl chloride. Compound 12 was reduced to R-(-)-B-trityl prolinamide,13, using sodium borohydride, acetic acid and dioxane. (Florvall, L., et al., J. Med. Chem. 25, 1280-86 (1982). The amine 12 was condensed with theacid 5 on the same basis as the synthesis of compound 6, to afford N-tritylbenzamide (14). Compound 14 was treated with hydrogen chloride in ethanol to give 15 in 65% yield. [α]D =-8.4° C. (C=1.4, MeOH), m.p. 200°-202° C. (hydrochloride salt), FT-IR (KBr) λ3390 (br, NH), 3300 (sharp, NH (amide)), 1660 (strong, C=O). 1H NMR (CDCI3) δ8.29 (br, NH), 7.95 (d, 1 H, J=1.95 Hz), 7.25 (d, 1H, J=1.99 Hz), 3.90 (s, 3H), 3.84 (s, 3H), 3.57 (m, 1H), 3.47 (m, 1H), 3.39 (m, 1H), 3.00 (m, 2H), 1.93 (m, 1H), 1.83 (m, 1H), 1.78 (m, 1H), 1.50 (m, 1H). Anal. calcd, for C14H20CIIO3N: C, H, N. Optical purity=100% retention time 8.75 mL (chiralcel OD, 10% ethanol/hexane, 1 mL/min).

Provenance & Evidence