Dicyclohexylcarbodiimide → HCID 22867564, compound

Participants

Reaction Steps

To a mixture of 0.198 g (0.69 mmol) of N-quinaldoyl-L-asparagine and 0.24 ml (1.38 mmol) of N,N-diisopropylethylamine in 1 ml of chloroform was added 0.146 g (0.71 mmol) of dicyclohexylcarbodiimide. The reaction mixture was stirred for 24 hr. at room terperature, then partitioned between 10ml of 5% sodium bicarbonate and 10 ml of ether. The aqueous phase was acidified to pH2 and the acid was taken up by extraction with chloroform (3×10ml). The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to give 0.101 g of crude product. This was recrystallized from a small portion of methylene chloride to give 0.06 g of the title compound melting at 144°-146° C.; NMR (5% DMSO-d6 in CDCl3): 3.22 (d, 2H, ala CH2); 4.95 (m, 1H, ala CH); 7.2-8.57 (m, 7H, aromatic, OH); 9.19(d, 1H, NH).

Provenance & Evidence