Potassium Carbonate → N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine

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Reaction Steps

5.6 g of N-palmitoylcysteine, 5 g of 1,2-epoxy-octadecene and 5.35 g of potassium carbonate in 100 ml ethanol are heated in an atmosphere of nitrogen at 80° for 15 hours. After evaporation, HCl is added so as to obtain a pH of about 3 and the mixture is extracted with chloroform. The chloroform extract is washed with water and is then dried with sodium sulfate. After evaporation there is obtained a colorless residue which is recrystallized from ethyl acetate. There are obtained colorless crystals of the N-palmitoyl-S-[2(R,S)-hydroxyoctadecyl]-(L)-cysteine of melting point 96°-98° [α]D20 =+16° (c=0.78, chloroform).

Provenance & Evidence