Sodium Bicarbonate → HCID 57384850, compound

Participants

Reaction Steps

A stirred solution of 11b (38 mg, 0.053 mmol.) in anhydrous tetrahydrofuran (10 ml) was cooled to 0° C. under a nitrogen atmosphere before adding a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (265 ul, 0.265 mmol.). The reaction mixture was warmed to room temperature and was stirred under a nitrogen atmosphere for 2.5 hours. The reaction mixture was then treated with saturated aqueous sodium bicarbonate solution (20 ml) and the subsequent mixture was extracted with ethyl acetate (3×15 ml). The combined extract was dried over sodium sulfate, filtered and evaporated. The residue was purified on a silica column eluting with 50% ethyl acetate, 50% hexane then 100% ethyl acetate to yield 11 as a colourless solid (15 mg, 47%). 1H NMR δ (300 MHz NMR, CDCl3) 0.81-0.92 (m, 3H) 0.93-1.01 (m, 4H), 1.34-1.39 (d, 3H, J=7.4 Hz), 1.45-2.10 (m, 6H), 2.18-2.20 (s, 1H), 2.38-2.53 (m, 2H), 2.55-2.71 (m, 2H), 2.75-2.92 (m, 2H), 3.18-3.30 (m, 2H), 3.51-3.53 (s, 3H), 3.54-3.60 (d, 1H, J=12.5 Hz), 4.09-4.40 (m, 4H), 4.50-4.60 (d, 1H, J=12.7 Hz), 5.43-5.69 (m, 3H), 5.91-6.00 (m, 3H), 6.51-6.58 (d, 1H, J=7.4 Hz), 6.68-6.78 (m, 2H), 6.80-6.90 (d, 1H J=8.7 Hz), 7.05-7.12 (t, 1H, J=7.7), 7.37-7.45 (d, 1H, J=9.6), 8.15-8.38 (bs, 1H). LCMS (m/z) 599.36 [M+H] Tr=4.59 min.

Provenance & Evidence