Acetic Acid → HCID 10168008, compound

Participants

Reaction Steps

Acetic acid (0.05 mL, 0.92 mmol) was added to a mixture of N-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (which was obtained in Example 10) (113 mg, 0.46 mmol), ethyl 2-[2,4-dioxo-5-[4-(4-oxo-1-piperidineyl)benzyl]-1,3-thiazolidin-3-yl}acetate (which was obtained in Example 50) (180 mg, 0.46 mmol), and DMF (3 mL). The mixture was stirred for 20 minutes and then, sodium triacetoxyborohydride (117 mg, 0.55 mmol) was added, and the new mixture was stirred at room temperature for 24 hours. The volatiles were removed in vacuo and the residue was purified by flash chromatography (dichloromethane/methyl alcohol 5/1) to produce an off-white solid (210 mg, 74% yield); mp 153-155° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.18 (t, J=7.1 Hz, 3H), 1.30-1.60 (m, 2H), 1.80-1.83 (m, 2H), 2.50-2.65 (m, 4H), 2.80-2.85 (m, 4H), 3.40 (m, 2H), 3.60 (m, 1H), 4.13 (q, J=7.1 Hz, 2H), 4.47 (m, 1H), 5.04 (m, 1H), 6.80-6.90 (m, 3H), 6.97 (m, 1H), 7.1 (m, 2H), 7.19 (m, 1H); MS (ES) m/z: 621 (MH+); Anal. Calcd. for: C28H36N4O8S2×1CH3CO2H: C, 52.93; H, 5.92; N, 8.23. Found: C, 52.69; H, 5.63; N, 8.23.

Provenance & Evidence