Reaktion #1552039

Reaktionsgleichung

trifluoroacetic acid

N-palmitoyloxy-glycyloxysuccinimide

L-histidine

triethylamine

→

colorless solid

Ausbeute 54.0%

N-palmitoyl-Gly-His TFA

Ausbeute 54.0%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooled with ice
2. 2
   workup.ADDITIONwas added
3. 3
   Temperaturwhile cooled with ice
4. 4
   workup.STIRRINGby stirring for another 17 hours
5. 5
   FiltrationThe precipitated solid was filtered off as it
6. 6
   Sonstigeto obtain a solid
7. 7
   workup.STIRRINGby stirring
8. 8
   Waschento be washed with 2 L of water three times
9. 9
   Sonstigewas subsequently dried under reduced pressure
10. 10
    SonstigeThe resulting dry solid
11. 11
    workup.DISSOLUTIONwas dissolved in 400 mL of trifluoroacetic acid
12. 12
    Filtrationa small amount of insoluble matter was filtered off with a membrane
13. 13
    Filtrationfilter
14. 14
    EinengenThe filtrate was concentrated under reduced pressure to about half the amount, which
15. 15
    Waschenwas then washed with diethyl ether
16. 16
    SonstigeThe solid was dried under reduced pressure
17. 17
    Waschenwas washed with water an appropriate number of times
18. 18
    Sonstigethe resulting solid was dried under reduced pressure

Vorschrift

198 g of the N-palmitoyloxy-glycyloxysuccinimide synthesized above as a whole was suspended in DMF and, to the resultant solution while cooled with ice with stirring, a suspension of 113 g (0.728 mol) of L-histidine, 55.6 mL (0.400 mol) of triethylamine, and 350 ml of water was added. Subsequently, the resultant solution was stirred for 30 minutes while cooled with ice, and the temperature was then raised to room temperature, followed by stirring for another 17 hours. The precipitated solid was filtered off as it was to obtain a solid. The resultant product was added to a mixed solution of 120 mL of trifluoroacetic acid and 1.5 L of ice water, followed by stirring and then filtering insoluble matter. The resulting solid was placed in a jug to be washed with 2 L of water three times, and was subsequently dried under reduced pressure. The resulting dry solid was dissolved in 400 mL of trifluoroacetic acid, and a small amount of insoluble matter was filtered off with a membrane filter. The filtrate was concentrated under reduced pressure to about half the amount, which was then washed with diethyl ether. The solid was dried under reduced pressure and was washed with water an appropriate number of times, and the resulting solid was dried under reduced pressure to obtain 112 g (54%) of a colorless solid.

Quelle