Water → Arachidonyl azide

Temperature

90 °C

To a magnetically stirred solution of 50 mg (0.17 mmol) of arachidonyl alcohol in 1 mL of pyridine was added 29.2 mg (0.225 mmol) of mesyl chloride at 0° C. After stirring for 5 hours, the reaction mixture was poured into 2 mL of cold water and extracted with diethyl ether (2×4 mL). The combined ether extracts were washed with 1 N sulfuric acid and saturated sodium bicarbonate solution and evaporated in vacuo. The crude mesylate was dissolved in 2 mL of anhydrous DMF, and then a solution of 6.5 mg (0.85 mmol) of sodium azide in 4 mL of anhydrous DMF was added at room temperature. The reaction mixture was heated to 90° C. for 24 hours behind a safety shield. The mixture was cooled to room temperature, inorganic material was filtered off, and the filtrate was poured into 1 mL of cold water. Extraction with diethyl ether (2×6 mL), drying (MgSO4), and evaporation gave an oily residue which was chromatographed on silica gel (petroleum ether) to afford 39 mg (73%) of arachidonyl azide as a colorless oil: 1H NMR (200 MHZ, CDCl3) δ 5.38 (m, 8H), 3.27 (t, J=6 Hz, 2H), 2.81 (m, 6H), 2.11–2.01 (m, 4H), 1.62 (m, 2H), 1.48–1.25 (m, 6H), 0.89 (t, J=7 Hz, 3H).

1. extractionextracted with diethyl ether (2×4 mL)
2. washThe combined ether extracts were washed with 1 N sulfuric acid and saturated sodium bicarbonate solution
3. customevaporated in vacuo
4. dissolutionThe crude mesylate was dissolved in 2 mL of anhydrous DMF
5. temperatureThe mixture was cooled to room temperature
6. filtrationinorganic material was filtered off
7. additionthe filtrate was poured into 1 mL of cold water
8. extractionExtraction with diethyl ether (2×6 mL)
9. customdrying
10. custom(MgSO4), and evaporation
11. customgave an oily residue which
12. customwas chromatographed on silica gel (petroleum ether)

ORD record

ord-98f42b6577db414c84291fa912228cd8

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07161016B1