Sodium Methoxide → HCID 9933752, compound

Participants

Reaction Steps

2-[4-(2-carboxy-2-methylpropyl)phenyl]-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (334 mg) was dissolved in methanol (10 ml) and sodium methoxide (324 mg) was added. The solution was heated to reflux for 4 hours, cooled and evaporated to dryness. The residue was partitioned between water (20 ml) and ethyl acetate (15 ml) and the organic layer was separated and washed with water (20 ml). The combined aqueous phases were acidified with 2M hydrochloric acid and extracted with ethyl acetate (3×25 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was triturated with isohexane to give 2-[4-(2-carboxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (117 mg); 1H NMR (d6 -DMSO): 1.1 (s, 6 H), 2.24 (s, 3 H), 2.85 (br, 2 H), 3.80 (s, 3 H); 7.13 (br, 2 H), 7.35 (br d, 2 H), 7.50 (br s, 1 H), 7.57 (q, 1 H), 8.78 (dd, 1 H), 10.41 (br s, 1 H); mass spectrum (+ve ESP) 457.2 (M+H)+.

Provenance & Evidence