Acetic Acid → N-[5-((1R)-2-{1-[4-(2,4-Dioxo-imidazolidine-1-sulfonyl)-phenyl]piperidin-4-ylamino}-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide

Participants

Reaction Steps

Acetic acid (0.15 mL, 2.6 mmol) was added dropwise into a mixture N-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (320 mg, 1.3 mmol), 1-[[4-(4-oxo-1-piperidinyl)phenyl]sulfonyl}-2,4-imidazolidinedione (440 mg, 1.3 mmol) and N,N-dimethylformamide (5 mL). The mixture was stirred for 20 minutes and then, sodium triacetoxyborohydride (331 mg, 1.56 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 4/1) to produce a white solid (496 mg, 67% yield): mp 200-202° C.; c 1.35-1.42 (m, 2H), 1.81-1.97 (m, 2H), 2.83-2.97 (m, 6H), 3.95-3.97 (m, 2H), 4.22 (s, 2H), 4.57-4.6 (m, 1H), 7.1 (M, 3H), 7.2 (m, 1H), 7.75 (m, 2H), 8.4 (brs, 2H); MS m/e 566 (M−H)+; Analysis for: C23H29N5O8S2 Calc'd: C, 48.67; H, 5.11; N, 12.34 Found: C, 47.64; H, 5.2; N, 11.26.

Provenance & Evidence