Hydrochloric Acid → HCID 178443806, compound

Participants

Reaction Conditions

Reaction Steps

30 g of N-octyloxycarbonyl-62 -alanine were dissolved in 300 ml of dimethylformamide and 1 molar equivalent of triethylamine. Next, 1 molar equivalent of 2-(5-norbornene-2,3-dicarboximido)-1,1,3,3-tetramethyluronium tetrafluoroborate was added. The mixture was then stirred for 1 hour at a temperature of 25° C. Next, a solution containing 1.2 molar equivalents of histidine and 1.2 molar equivalents of sodium hydroxide in 100 ml of water were added dropwise, while keeping the temperature below 30° C. After stirring for 6 hours, the mixture was neutralized with 1 molar equivalent of 5N hydrochloric acid, followed by 100 ml of water. After stirring for 30 minutes, the mixture was poured into 2 liters of acetone. The white precipitate formed was filtered off and dried. The crude product was dissolved in 10 ml/g of refluxing 96% ethanol. The solution was filtered while hot and the product then crystallized at room temperature. After processing the precipitate, 29.4 g of a white crystalline product were obtained (63% yield).

Provenance & Evidence