Sodium Bicarbonate → N-5,6,7,8-tetrahydro-1-naphthoyl-alpha-L-glutamyl-5-aminopyridine-2-carbonitrile

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Reaction Steps

A solution of 1.91 g (0.009 mol) of 5,6,7,8-tetrahydro-1-naphthoyl chloride in anhydrous tetrahydrofuran (50 cm3) is added dropwise to a solution of 1.5 g (0.0064 mol) of alpha-L-glutamyl-5-aminopyridine-2-carbonitrile and 5.05 g (0.06 mol) of NaHCO3 in 50 cm3 of water. After stirring for 15 minutes at 20 C., the tetrahydrofuran is removed under vacuum and the remaining aqueous solution is acidified to pH 2-3 with a 6 N solution of HCl to give a precipitate of 1.4 g of N-5,6,7,8-tetrahydro-1-naphthoyl-alpha-L-glutamyl-5-aminopyridine-2-carbonitrile (yield: 55%, melting point: 141° C. in the amorphous state) after filtration and trituration in hexane. The sweetening potency of this compound, on a weight basis, is approximately 40,000 (forty thousand) times that of sucrose by comparison with a 2% solution of sucrose, 30,000 (thirty thousand) times by comparison with a 5% solution of sucrose and 20,000 (twenty thousand) times by comparison with a 10% solution of sucrose. This is tantamount to saying that an aqueous solution of 5 mg/1 of the compound has an intense sweet taste equivalent to that of a 10% solution of sucrose, corresponding to the sweetening intensities generally used in food preparations.

Provenance & Evidence