Ethanolamine → Dodecyl 2-((2-hydroxyethyl)amino)propanoate

To a stirred solution of 3 (1 g, 3.2 mmol) in acetonitrile/water (5:5 mL) was added sodium bicarbonate (0.262 g 3.2 mmol) and followed by ethanol amine (0.5 mL, 0.5 vol) at 25-30° C. The reaction mixture was stirred for 12 h at RT; the reaction was monitored by TLC. The solid obtained in the reaction mixture was filtered under vacuum, the solvent concentrated, diluted with ethyl acetate/water and stirred for 15 minutes at 25-30° C. The aqueous and organic layers were separated, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 64 (0.9 g, yield: 95%) as a liquid

1. customThe solid obtained in the reaction mixture
2. filtrationwas filtered under vacuum
3. concentrationthe solvent concentrated
4. additiondiluted with ethyl acetate/water
5. stirringstirred for 15 minutes at 25-30° C
6. customThe aqueous and organic layers were separated
7. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
8. washThe combined organic layers were washed with brine solution
9. dry with materialThe organic layer was dried over Na2SO4
10. concentrationconcentrated under vacuum

ORD record

ord-fdd7208ff0a44b31b55a203d930da667

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08900625B2