Lithium Hydroxide → HCID 57987346, compound

Participants

Reaction Steps

A solution of LiOH (10 mg, 0.42 mmol) in water (0.5 ml) was added to a stirred solution of the ester (Step 3, 42 mg, 0.074 mmol) in THF (1 ml) at RT. The reaction was stirred at RT O/N then quenched with 2N HCl (1 ml). The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (×2). The combined extracts were washed with brine (×1), dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 2-8% MeOH/DCM) to give the acid (22 mg) as a colourless solid. 1H NMR (400 MHz, CD3OD): δ 0.60-0.70 (1H, m), 0.82-1.02 (7H, m), 1.14-1.24 (1H, m), 1.38-1.49 (2H, m), 1.72-1.75 (1H, m), 1.84-1.95 (4H, m), 2.18-2.20 (2H, m), 2.52 (1H, brt, J 11), 2.82 (1H, brd, J 11), 3.53 (1H, dd, J 9.8, 4.0), 3.87 (1H, brd, J 10), 7.45 (2H, d, J 8.2), 7.52 (2H, t, J 7.6), 7.64 (1H, J 7.4), 7.70-7.80 (8H, m); M/Z (ES+) 552 (MH+).

Provenance & Evidence