Nicotinic Acid → 3-Pyridinecarbonyl chloride, hydrochloride (1:1)

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Reaction Steps

1.5 g of nicotinic acid were heated to reflux in 1.8 ml of thionyl chloride for one and a half hours. After taking up in toluene and evaporating, the residue was triturated with ether, then dried to obtain 2.12 g of nicotinoyl chloride hydrochloride. 258 mg of the E isomer of Step B of Example 1 were dissolved in 1 ml of pyridine, and 93 mg (0.525 mM) of the freshly prepared nicotinoyl chloride hydrochloride were added and stirred for 2 hours under an inert atmosphere. After diluting with 10 ml of methylene chloride, washing with 1N hydrochloric acid and then with a solution of sodium bicarbonate, drying and evaporating, the residue was chromatographed over silica and eluted with a mixture of methylene chloride and acetone (9-1) to obtain 232 mg of 1,1-dimethylethyl (6S,7S) 7-[2-(2-trityl-aminothiazol-4-yl)-2-(Z)-(methoxyimino)-acetamido]-3-[(3-nicotinoyloxy)-1-(E)propenyl]-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate.

Provenance & Evidence