Реакция #1552039

Уравнение реакции

trifluoroacetic acid

N-palmitoyloxy-glycyloxysuccinimide

L-histidine

triethylamine

→

colorless solid

Выход 54.0%

N-palmitoyl-Gly-His TFA

Выход 54.0%

Растворители

DMF

water

Условия реакции

Обработка

1. 1
   Температураwhile cooled with ice
2. 2
   workup.ADDITIONwas added
3. 3
   Температураwhile cooled with ice
4. 4
   workup.STIRRINGby stirring for another 17 hours
5. 5
   ФильтрацияThe precipitated solid was filtered off as it
6. 6
   Другоеto obtain a solid
7. 7
   workup.STIRRINGby stirring
8. 8
   Промывкаto be washed with 2 L of water three times
9. 9
   Другоеwas subsequently dried under reduced pressure
10. 10
    ДругоеThe resulting dry solid
11. 11
    workup.DISSOLUTIONwas dissolved in 400 mL of trifluoroacetic acid
12. 12
    Фильтрацияa small amount of insoluble matter was filtered off with a membrane
13. 13
    Фильтрацияfilter
14. 14
    КонцентрированиеThe filtrate was concentrated under reduced pressure to about half the amount, which
15. 15
    Промывкаwas then washed with diethyl ether
16. 16
    ДругоеThe solid was dried under reduced pressure
17. 17
    Промывкаwas washed with water an appropriate number of times
18. 18
    Другоеthe resulting solid was dried under reduced pressure

Методика

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.

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