12-Bromododecanoic Acid → 12-Chloro-dodecanoic acid

To 12-bromododecanoic acid (1 g) dissolved in acetonitrile (50 ml) was added calcium chloride (2 g) and tetra-n-butylammonium chloride (1.2 g), and the mixture was heated under reflux for 4 hours. The reaction mixture was filtered, concentrated and distributed into ethyl acetate-water, and the ethyl acetate layer was dried over anhydrous sodium sulfate to give 12-chlorododecanoic acid. After a 280 mg portion of 12-chlorododecanoic acid thus obtained, para-nitrophenol (167 mg) and N,N'-dicyclohexylcarbodiimide (245 mg) in N,N-dimethylformamide (DMF) was stirred for 12 hours, precipitates were removed by filtration and DMF was removed by distillation to give an active ester. To the active ester of 12-chlorododecanoic acid dissolved in DMF were added 6-(4'-N-glycyl-spicaminyl-amino)purine hydrochloride (456 mg) and triethylamine (1.2 ml ), and the mixture was stirred for 12 hours. The reaction mixture was concentrated and subjected to chromatography on a silica gel column with eluent systems of chloroform-methanol (from 7:1 to 5:1) to give SPK132 in the yield of mg.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 4 hours
3. filtrationThe reaction mixture was filtered
4. concentrationconcentrated
5. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate

ORD-Eintrag

ord-33ca184a83ca4e71846276d2b3bde25d

Quelldatensatz

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05461036