Ethanolamine → Capric monoethanolamide

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).

1. filtrationfiltered
2. concentrationThe filtered solution was concentrated in vacuo
3. additionThe residue was diluted with ethyl acetate (300 ml)
4. washwashed with 0.1% HCl (50 ml×3), saturated NaHCO3 (50 ml×3), brine (50 ml), and water (50 ml)
5. dry with materialThe organic solution was dried over MgSO4 and solvent
6. customwas removed on a rotovap
7. customThe crude product was purified by flash column chromatography
8. washeluting with a gradient of dichloromethane/methanol (95:5) to dichloromethane/methanol (9:1)

ORD record

ord-c609ca05171c4b08beec8c0063edeb93

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205261B2