反应详情

To a solution of material from Example 59 (3.4 g, 10.20 mmol) in a mixture of THF (30 mL) and acetic acid (5.00 mL) is added sodium acetate (1.004 g, 12.24 mmol) followed by 2-bromomalonaldehyde (1.540 g, 10.20 mmol). The resulting mixture is stirred at room temp for 18 h, then filtered thru a ground glass frit and the filtrate is concentrated in vacuo. The resulting residue treated with EtOAc, filtered thru a ground glass frit and the filtrate is extracted with sodium bicarbonate, water, brine, dried over Na2SO4, filtered and evaporated to dryness. The residue is purified by BIOTAGE® Silica gel chromatography on an 80 g Thompson Single Step silica cartridge using a linear gradient from 30% EtOAc/hexanes to 100% EtOAc over 11.25 column volumes to give 960 mg (29.7%) of the title compound as a yellow solid. LC/MS (Condition A): ret. T=2.92 min, (M+Na)+ 308.13. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.64 (1 H, s), 8.83-8.98 (1 H, m), 8.06 (1 H, s), 6.89 (1 H, t, J=5.40 Hz), 3.31 (2 H, d, J=5.27 Hz), 2.99 (2 H, q, J=6.69 Hz), 1.69 (2 H, t, J=7.03 Hz), 1.39 (9 H, s).

1. filtrationfiltered thru a ground glass frit
2. concentrationthe filtrate is concentrated in vacuo
3. additionThe resulting residue treated with EtOAc
4. filtrationfiltered thru a ground glass frit
5. extractionthe filtrate is extracted with sodium bicarbonate, water, brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe residue is purified by BIOTAGE® Silica gel chromatography on an 80 g Thompson Single Step silica cartridge