Sodium Bicarbonate → HCID 57384590, compound

Participants

Reaction Steps

A stirred solution of 8d (90 mg, 0.108 mmol.) in anhydrous tetrahydrofuran (30 ml) was cooled over an ice bath before adding a solution of tetra-n-butylammonium fluoride (1M in tetrahydrofuran, 1.08 ml, 1.08 mmol.). The reaction was warmed to room temperature and stirred for 1 hour before adding saturated sodium bicarbonate solution (25 ml). The mixture was extracted with ethylacetate (2×25 ml). The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a brown gum. The gum was purified on a silica column eluting with ethyl acetate to yield 8 as a white solid (27 mg) LCMS. (m/z) 607.27 [M+H] Tr=4.21 min 1H NMR δ (300 MHz NMR, CDCl3) 1.12-1.28 (m, 6H), 1.31-1.39 (d, 3H, J=7.1 Hz), 1.44-1.60 (m, 3H), 1.71-2.13 (m, 3H) 2.14-2.28 (m, 1H), 2.38-2.70 (m, 4H), 2.81-2.91 (m, 1H), 2.91-3.08 (m, 1H), 3.61-3.70 (d, 1H), 4.12-4.21 (m, 1H), 4.32-4.46 (m, 2H), 4.81-4.89 (s, 1H) 5.07-5.18 (q, 1H, J=6.5 Hz), 5.90-6.05 (m, 1H) 6.15-6.33 (m, 3H) 6.37-6.44 (d, 1H) 6.61-6.70 (m, 1H) 6.95-7.72 (m, 7H) 7.80-8.05 (bs, 1H).

Provenance & Evidence