Pyridine → HCID 86701277, compound

Participants

Reaction Conditions

Reaction Steps

Acetyl chloride (9 μL, 0.125 mmol) was added to a solution of (3S,6S,7R,8R)-8-(cyclohexylmethyl)-3-(3-hydroxy-4-methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (50 mg, 0.100 mmol) and pyridine (40 μL, 0.480 mmol) in CH2Cl2 (1 mL), and the reaction was stirred at ambient temperature (about 22° C.) overnight. The solution was loaded directly onto a pre-packed SiO2 column for purification by column chromatography (0→30% EtOAc/CH2Cl2) to afford the title compound (28 mg, 52%) as a white solid: mp 164-170° C.; 1H NMR (400 MHz, CDCl3) δ 8.70 (d, J=7.5 Hz, 1H), 8.35 (d, J=5.4 Hz, 1H), 7.03 (d, J=5.5 Hz, 1H), 5.47 (br s, 1H), 5.25-5.11 (m, 1H), 5.03 (t, J=9.9 Hz, 1H), 4.97-4.84 (m, 1H), 3.92 (s, 3H), 3.72 (br s, 1H), 2.69 (dd, J=16.8, 7.0 Hz, 1H), 2.60 (sept, J=14.0, 7.0 Hz, 1H), 2.40 (s, 3H), 1.83-1.54 (m, 6H), 1.36-1.02 (m, 14H), 0.94-0.67 (m, 2H); HRMS-ESI (m/z): calcd for C28H38N2O10, 562.2526; found, 562.2516.

Provenance & Evidence