Acetic Acid → N-[2-[2-(4-Hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

Participants

Reaction Steps

N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide (Example 9c), 0.12 g) was dissolved in methanol (5 mL) and treated with 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.32 g), acetic acid (0.1 mL) and water (0.3 mL). The resultant mixture was stirred for 2 hours and then sodium cyanoborohydride (0.01 g) was added and the reaction mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in methanol (5 mL) and adsorbed onto silica gel. The product was purified by flash chromatography eluting with 5% methanol, 1% ammonia in dichloromethane. Collected fractions were concentrated and the resultant residue was taken up in dichloromethane (5 mL) and treated with 4N hydrogen chloride in dioxane (0.2 mL). The mixture was stirred vigorously and concentrated. The resulting gum was azeotroped with dichloromethane (3×5 mL) to give the titled compound (0.13 g) as a white solid.

Provenance & Evidence