Triethylamine → N-docosahexaenoyl-D-alanine

温度

0 °C

4-hydroxyphenyldimethylsulfomethyl sulfate 2.66 g (0.01 mol) was heated and dissolved in 40 ml of acetonitrile. Docosahexaenoic acid 3.28 g (0.01 mol) was added to the solution obtained in a stream of nitrogen, and the mixture was stirred at 0° C. To the mixture solution, dicyclohexyl carbodiimide 2.06 g (0.01 mol) was added little by little, and the solution was stirred for 2 hours at 0° C. and then for 2 hours at room temperature. The solution reacted was filtered to remove dicyclohexyl urea, and the filtrate was distilled in vacuo to obtain oily residue. D-alanine 0.89 g (0.01 mol) and triethyl amine 1.4 ml (0.01 mol) were added to 10 ml of water. An acetonitrile solution of the above oily residue was added to the mixture with stirring, and stirred for 10 hours at room temperature. After reaction, the reaction mixture was concentrated under reduced pressure. The concentrate was adjusted to pH 2 or 3 with 6N-HCl, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium acetate, and freed of solvent in vacuo. The oily residue obtained was purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel and N-docosahexaenoyl-D-alanine 1.6 g was obtained.

1. customobtained in a stream of nitrogen
2. stirringwas stirred for 2 hours at 0° C.
3. customThe solution reacted
4. filtrationwas filtered
5. customto remove dicyclohexyl urea
6. distillationthe filtrate was distilled in vacuo
7. customto obtain oily residue
8. stirringwith stirring
9. stirringstirred for 10 hours at room temperature
10. customAfter reaction
11. concentrationthe reaction mixture was concentrated under reduced pressure
12. extractionextracted with ethyl acetate
13. washThe ethyl acetate layer was washed with water
14. dry with materialdried over anhydrous sodium acetate
15. customThe oily residue obtained
16. customwas purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel

ORDレコード

ord-d2b60b2460444db88738c8a8c12cf7c8

出典データセット

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05112863