Acetyl chloride → HCID 56848036, compound

Participants

Reaction Steps

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; 94.4 mg, 0.175 mmol) in pyridine (2 mL) was treated with acetyl chloride (70 μL, 0.98 mmol), and the mixture was allowed to stir at room temperature for 2.5 h. The mixture was then evaporated at room temperature under vacuum to a smaller volume. The concentrate was diluted with EtOAc and washed with 1 N HCl. The aqueous layer was extracted 3 times with EtOAc. The organic fractions were combined and dried with anhydrous MgSO4. The solvent was then evaporated at room temperature under vacuum. The resulting crude material was purified by silica gel chromatography (eluting with 50% EtOAc in Hexane going to 90% EtOAc in Hexane in a single step). The title product (96.8 mg, 95%) was isolated as a colorless semi-solid: 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 8.16 (d, J=8.4 Hz, 2H), 7.87-7.69 (m, 2H), 7.39 (d, J=8.1 Hz, 4H), 5.19 (dd, J=9.3, 6.6 Hz, 2H), 4.71 (d, J=16.1 Hz, 1H), 3.70-3.28 (m, 12H), 3.12 (dd, J=9.2, 7.9 Hz, 1H), 2.24 (s, 3H), 1.60 (s, 1H); 13C NMR (101 MHz, CDCl3) δ 163.17, 141.89, 135.74, 129.76, 128.21, 126.89, 122.44, 121.26, 81.74, 79.82, 73.74, 69.61, 60.33, 58.86, 58.10, 21.05, 18.12; ESIMS m/z 581 (M+H).

Provenance & Evidence