N-(2-hydroxyethyl)decanamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethanolamine (3.42 ml, 56.6 mmol) and triethylamine (5.51 ml, 39.5 mmol) in dry tetrahydrofuran (150 ml) was cooled in ice bath and decanoyl chloride (5.44 ml, 26.3 mmol) in tetrahydrofuran (50 ml) was added dropwise. The reaction mixture was stirred at room temperature overnight and filtered. The filtered solution was concentrated in vacuo. The residue was diluted with ethyl acetate (300 ml) and washed with 0.1% HCl (50 ml×3), saturated NaHCO3 (50 ml×3), brine (50 ml), and water (50 ml). The organic solution was dried over MgSO4 and solvent was removed on a rotovap. The crude product was purified by flash column chromatography, eluting with a gradient of dichloromethane/methanol (95:5) to dichloromethane/methanol (9:1) to give 5.57 g of a white solid NAE-10:0 (99% yield): Rf=0.35 in dichloromethane/methanol (95:5); 1H NMR (CDCl3) 6 6.11 (br, 1H), 3.72 (m, 2H), 3.42 (m, 2H), 3.08 (br, 1H), 2.20 (t, J=7.9 Hz, 2H), 1.64 (m, 2H), 1.26–1.29 (m, 12H), 0.88 (t, J=6.8 Hz, 3H); FT-IR (Table 1). filtered The filtered solution was concentrated in vacuo The residue was diluted with ethyl acetate (300 ml) washed with 0.1% HCl (50 ml×3), saturated NaHCO3 (50 ml×3), brine (50 ml), and water (50 ml) The organic solution was dried over MgSO4 and solvent was removed on a rotovap The crude product was purified by flash column chromatography eluting with a gradient of dichloromethane/methanol (95:5) to dichloromethane/methanol (9:1)