Potassium Carbonate → N-[4-[4-[Ethyl(5-hydroxy-5-methylhexyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide

Participants

Reaction Steps

A stirred mixture of the product from Example 25 (0.92 g, 2.08 mmol) and 17.2 mL of a solution of potassium carbonate (5 g) in MeOH (80 mL) and water (20 mL) was refluxed, under nitrogen for 24 h. An additional 17.2 mL of the potassium carbonate solution was added and reflux was continued for 24 h. The mixture was then concentrated to remove MeOH and the aqueous residue was adjusted to pH 8 and washed with EtOAc. The aqueous solution was then concentrated to dryness, and the solid residue was extracted with CH2Cl2. This extract was concentrated and the residue was chromatographed on silica gel with 10% MeOH--1% NH4OH-CHCl3 to give 0.292 g (35.1%) of the titled product, a compound of Formula I': NMR (CDCl3) δ1.09 (t, 3H), 1.21 (s, 6H), 1.53 (m, 9H), 1.97 (m, 1H), 2.55 (m, 6H), 2.94 (s, 3H), 4.61 (m, 1H), 7.15 (d, 2H), 7.35 (d, 2H); MS m/z (relative intensity) 400 (M+, 17.4), 385 (14.5), 367 (11.1), 321 (36.6), 299 (92.8), 172 (100).

Provenance & Evidence