Thionyl Chloride → Lysine dihydrochloride

Participants

Reaction Steps

11.9 g of thionyl chloride are added in the cold to L-lysine hydrochloride (11 g) in 100 ml of ethanol and the mixture is refluxed for 3 h. After evaporation of the excess thionyl chloride and ethanol, the product is washed with heptane and then dried under vacuum to give 14.8 g of lysine bishydrochloride in which the acid group is esterified with ethanol. This product (4.9 g) is reacted with 7 g of the N-hydroxysuccinimide derivative of palmitic acid (Rn Cas 14464-31-4, available from Sigma) in an acetone/water mixture (80+40 ml respectively), in the presence of 7 g of triethylamine. After one night at room temperature, the product is precipitated by adding 1 N hydrochloric acid. After purification by passage over a silica column, 3.3 g of the desired product are recovered. Its structure is confirmed by NMR spectroscopy.

Provenance & Evidence