Reaktion #323692

Reaktionsgleichung

3-hexadecanoyloxyoctadecanoic acid

L-threonyl-L-threonine

triethylamine

→

N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-threonine

Lösungsmittel

tetrahydrofuran water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter removal of tetrahydrofuran under reduced pressure
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe extract was washed with water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give a residue which
7. 7
   Sonstigewas purified by column chromatography on silica gel
8. 8
   WaschenElution
9. 9
   workup.ADDITIONwith a mixture of chloroform and methanol (20:1)

Vorschrift

A solution of N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (1.5 g) prepared by the method of Example 8 (1), L-threonyl-L-threonine (0.7 g) and triethylamine (0.44 ml) in tetrahydrofuran water (100 ml-200 ml) was stirred at room temperature for 5 hours. After removal of tetrahydrofuran under reduced pressure, the residue was acidified with 1% hydrochloric acid (100 ml) and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and concentrated to give a residue which was purified by column chromatography on silica gel. Elution with a mixture of chloroform and methanol (20:1) afforded N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-threonine (1.2 ) as powder.

Quelle