Chloroform → HCID 19047210, compound

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Reaction Steps

12-Hydroxydodecanoic acid (1 g) was dissolved in methylene chloride (25 ml), and triethylamine (2 ml) was added to the solution. To the mixture, while it was ice-cooled and stirred, was added dropwise 1-propanesulfonyl chloride (1.03 ml). After 1.5 hours of stirring, the reaction mixture was distributed into chloroform and water, and the chloroform layer was dried with anhydrous sodium sulfate and concentrated. The residue thus obtained was subjected to chromatography on a silica gel column with an eluent system of chloroform-hexane (2:1) to give 12-propanesulfonyloxydodecanoic acid (1.49 g). The product (210 mg) was dissolved in N,N-dimethylformamide (DMF). N-Hydroxysuccinimide (75 mg) and N,N'-dicyclohexylcarbodiimide (148 mg) were added, and the mixture was stirred for 12 hours. The precipitates obtained were removed by filtration and the filtrate was concentrated to give the active ester of 12-propanesulfonyloxydodecanoic acid. The active ester was dissolved in DMF, and 6-(4'-N-glycyl-spicaminyl-amino)purine hydrochloride (250 mg) and triethylamine (0.73 ml) were added. The mixture was stirred for 12 hours. The reaction mixture was concentrated, and the residue was subjected to chromatography on a silica gel column with an eluent system of chloroform-methanol (6:1) to give SPK230 in the yield of 480 mg.

Provenance & Evidence