Hydrochloric Acid → N-20:4 L-Serine MeEster

Temperature

-15 °C

Arachidonic acid (152 g, 0.5 mmol) and triethylamine (52 mg, 0.51 mmol) were dissolved in 3 ml of dry acetonitrile and chilled to −15° C., and 70 mg (0.51 mmol) of butyl chloroformate was added. After 30 min, the mixture free of the precipitated triethylamine hydrochloride was pipetted in a solution of L-serine methyl ester hydrochloride (156 mg, 1 mmol) and 0.14 ml of triethylamine in 1 ml of methanol, stirring was continued for 15 min at −15° C., then that mixture was allowed to warm to room temperature. After 2 h, 0.5 M HCl was added, and the mixture was extracted with ether (20 ml). The extract was washed with water, then dried with Na2SO4, and evaporated in vacuo. The residue was dissolved in 2 ml of chloroform and purified by column (2×2 cm) chromatography on aluminum oxide (basic, Brockmann II). Elution of the column with chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions gave 186 mg (95%) of desired N-arachidonoyl-L-serine methyl ester as oil: TLC (system A) Rf 0.5.

1. waitwas continued for 15 min at −15° C.
2. temperatureto warm to room temperature
3. waitAfter 2 h
4. extractionthe mixture was extracted with ether (20 ml)
5. washThe extract was washed with water
6. dry with materialdried with Na2SO4
7. customevaporated in vacuo
8. dissolutionThe residue was dissolved in 2 ml of chloroform
9. custompurified by column (2×2 cm) chromatography on aluminum oxide (basic, Brockmann II)
10. washElution of the column
11. customwith chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions

ORD record

ord-494d0ea2e7c84df993f72f8e3a0e7894

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274747B1