Water → HCID 21709352, compound

Participants

Reaction Steps

2.5 g of Raney nickel are added to 50 ml of water. With stirring, 4.5 g of sodium hydroxide are added so rapidly thereto that the water does not quite boil over, and the whole is then stirred for half an hour. 320 mg (0.48 mmol, MW 671.2) of N′,N′-bis(2-cyanoethyl)-N,N-dioctadecylethylenediamine are taken up in 500 ml of 0.5M potassium hydroxide solution (in EtOH/water 95:5 v/v). The activated Raney nickel is separated from the supernatant by decanting and is added to the starting solution. The whole is then hydrogenated for 24 hours using a hydrogenation plant. After removing the solvent by rotary evaporation, the residue is dissolved in 5 ml of methylene chloride. 500 mg (2.02 mmol, MW 246.27) of O-(tert-butoxycarbonyl)-phenylglyoxylic acid nilrile oxime (BOC-ON) are added thereto and the whole is stirred at room temperature for 24 hours. Subsequently, concentration by rotary evaporation is carried out. The crude product is purified by flash chromatography. The product is then taken up in 10 ml of a 1:3 v/v mixture of trifluoroacetic acid and methylene chloride. After 2 to 3 hours, the whole is subject to rotary evaporation and dried for 0.5 hours under a high vacuum. Finally, lyophilisation from butanol/water (1:1 v/v) is carried out

Provenance & Evidence