反応 #1552039

反応方程式

trifluoroacetic acid

N-palmitoyloxy-glycyloxysuccinimide

L-histidine

triethylamine

→

colorless solid

収率 54.0%

N-palmitoyl-Gly-His TFA

収率 54.0%

溶媒

DMF

water

反応条件

後処理

1. 1
   温度while cooled with ice
2. 2
   workup.ADDITIONwas added
3. 3
   温度while cooled with ice
4. 4
   workup.STIRRINGby stirring for another 17 hours
5. 5
   ろ過The precipitated solid was filtered off as it
6. 6
   その他to obtain a solid
7. 7
   workup.STIRRINGby stirring
8. 8
   洗浄to be washed with 2 L of water three times
9. 9
   その他was subsequently dried under reduced pressure
10. 10
    その他The resulting dry solid
11. 11
    workup.DISSOLUTIONwas dissolved in 400 mL of trifluoroacetic acid
12. 12
    ろ過a small amount of insoluble matter was filtered off with a membrane
13. 13
    ろ過filter
14. 14
    濃縮The filtrate was concentrated under reduced pressure to about half the amount, which
15. 15
    洗浄was then washed with diethyl ether
16. 16
    その他The solid was dried under reduced pressure
17. 17
    洗浄was washed with water an appropriate number of times
18. 18
    その他the resulting solid was dried under reduced pressure

実験手順

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.

出典