Triethylamine → HCID 178513962, compound

Participants

Reaction Steps

In 27 ml of DMF was dissolved 2.18 g of L-histidyl-L-prolinamide dihydrobromide (4). The solution was cooled to -15° to -10° C. and 1.63 ml of triethylamine was added thereto. After reacting at this temperature for 20 minutes, the formed precipitates were filtered off to obtain a solution of L-histidyl-L-prolinamide. The solution was immediately used for the following synthesis. In a mixture of 14 ml of DMF and 14 ml of methylene chloride were dissolved 868 mg of compound (20 ) and 859 mg of HOBT and, 1.31 g of DCC was added to the solution under ice cooling. The mixture was reacted for 40 minutes. To the reaction mixture was added the foregoing DMF solution of L-histidyl-L-prolinamide. The reaction was performed at 0° to 4° C. overnight. The precipitates were filtered off and the filtrate was concentrated to dryness. The residue was subjected to column chromatography using silica gel. By eluting with chloroform-methanol-conc. ammonia water (80:20:2), 610 mg of Nα -(2-oxo-1-azetidinylacetyl)-L-histidyl-L-prolinamide (21) was obtained.

Provenance & Evidence