Succinic anhydride → HCID 56848038, compound

Participants

Reaction Steps

To a solution of N-{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamine (3; 140 mg, 0.26 mmol) in pyridine (5 mL) was added succinic anhydride (large excess), and the mixture stirred at room temperature for 3.5 h. The mixture was diluted with EtOAc and washed with 1 N HCl. The aqueous fraction was extracted with EtOAc (2×). The organic fractions were combined, washed with brine, dried with anhydrous MgSO4 and evaporated at room temperature under vacuum. The resulting crude material was purified by silica gel chromatography (eluting with 80% EtOAc in Hexane going to 100% EtOAc over a short gradient). The title product (64 mg, 39%) was isolated as a white solid: mp 61-75° C.; 1H NMR (300 MHz, CDCl3) δ 8.63 (s, 1H), 8.16 (d, J=8.3 Hz, 2H), 7.93-7.68 (m, 2H), 7.40 (d, J=8.4 Hz, 4H), 5.40-5.10 (m, 2H), 4.76 (d, J=16.1 Hz, 1H), 3.73-3.25 (m, 13H), 3.15 (dd, J=9.1, 7.9 Hz, 1H), 3.04-2.60 (m, 4H), 1.27 (dd, J=9.8, 4.3 Hz, 3H); ESIMS m/z 639 (M+H), 638 (M+).

Provenance & Evidence