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ChemicalBook CAS DataBase List (Z)-N-(1,3-dihydroxyoctadecan-2-yl)octadec-9-enamide
54422-45-6

(Z)-N-(1,3-dihydroxyoctadecan-2-yl)octadec-9-enamide synthesis

1synthesis methods
-

Yield:54422-45-6 75%

Reaction Conditions:

in tetrahydrofuran;

Steps:

2 Preparation of 2-oleoylamino-1,3-octadecanediol

EXAMPLE 2 Preparation of 2-oleoylamino-1,3-octadecanediol 3 ml of ethyl chloroformate (31 mmol) in 5 ml of tetrahydrofuran are solubilized in a round-bottomed flask under an inert atmosphere; this solution being cooled to -15° C., 11.3 g of triethylamine oleate (29.5 mmol) previously solubilized in 10 ml of tetrahydrofuran, are added dropwise. After stirring for 2 hours at room temperature, the reaction mixture is slowly poured, under an inert atmosphere, into 8.9 g of (D,L)-2-amino-1,3-octadecanediol prepared in the 1st stage of Example 1 (29.5 mmol) solubilized in 40 ml of tetrahydrofuran at 30° C. After stirring for 1 hour at 30° C., under an inert atmosphere, (thin layer chromatography on silica gel, eluent methylene chloride/methanol/ammonium hydroxide 15/3.5/0.6), the reaction mixture is washed with water and then evaporated to dryness under vacuum. The crude product obtained is chromatographed on a silica column (eluent: ethyl acetate/heptane 5/3) and 12.5 g of white crystals (yield 75%) are obtained after evaporation of the solution solvent under vacuum.

References:

US5618523,1997,A

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