Reaction #1857564

Reaction equation

3-hydroxy-N-((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)-4-methoxypicolinamide

acetyl chloride

→

title compound

Yield 90.4%

2-(((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)carbamoyl)-4-methoxypyridin-3-yl acetate

Yield 90.4%

Solvents

DCM

Conditions

Workup

1. 1
   workup.ADDITIONtreated with Celite® (3 scoopula tip-fulls)
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   Otherpurified

Procedure

To a solution of 3-hydroxy-N-((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)-4-methoxypicolinamide (75 mg, 0.166 mmol) were added TEA (34.8 μL, 0.250 mmol) and acetyl chloride (17.8 μL, 0.250 mmol) in DCM (0.832 mL). The reaction was stirred at room temperature for 4 h and then treated with Celite® (3 scoopula tip-fulls). The solvent was removed under reduced pressure and the resulting adsorbed material was directly loaded onto a column and purified using flash column chromatography (24 g SiO2, 0→100% EtOAc/hexanes) to afford the title compound (74 mg, 0.150 mmol, 90%) as a white powder (hygroscopic): IR (thin film): 3383, 2953, 2871, 1772, 1737, 1678, 1506, 1197, 1173 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J=8.2 Hz, 1H), 8.33 (d, J=5.4 Hz, 1H), 7.00 (d, J=5.4 Hz, 1H), 4.74 (dq, J=9.9, 6.3 Hz, 1H), 4.65-4.53 (m, 1H), 3.90 (s, 3H), 3.52 (app dt, J=8.9, 6.4 Hz, 1H), 3.31-3.22 (m, 1H), 3.15 (app dt, J=8.9, 6.6 Hz, 1H), 2.43-2.30 (m, 4H), 2.22-2.07 (m, 1H), 1.96-1.84 (m, 1H), 1.83-1.69 (m, 1H), 1.68-0.98 (m, 12H), 0.96-0.84 (m, 10H); HRMS-ESI m/z [M+H]+ calcd for: C26H41N2O7, 493.2908; found 493.2936.

Source