HCID 15599536, compound → 16452-52-1

Participants

Reaction Conditions

Reaction Steps

(S)-(+)-2-Acetoxyhexadecanoic acid (0.5 g; prepared by the method described in Agric. Biol. Chem., 54(12), 3337-3338, 1990) was dissolved in a solution of potassium hydroxide (1.0 g) in 50% aqueous ethanol was stirred at 70° C. for 2 hours. After the ethanol was evaporated, the reaction mixture was acidified with citric acid and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated to give (S)-(-)-2-hydroxyhexadecanoic acid (407 mg). The product was dissolved in DMF (20 ml), and N-hydroxysuccinimide (173 mg) and N,N'-dicyclohexylcarbodiimide (310 mg) were added to the solution. The mixture was stirred at room temperature for 12 hours and then filtered. 6-(4'-N-Glycyl-spicaminyl-amino)purine hydrochloride (0.60 g) and triethylamine (1.0 ml) were added to the filtrate, and the mixture was stirred for 12 hours, concentrated and subjected to chromatography on a silica gel column with eluent systems of chloroform-methanol (from 7:1 to 5:1) to give SPK271 in the yield of 97 mg. Substantially no contamination of the diastereomer was observed.

Provenance & Evidence