반응 #323684

반응 방정식

dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)-L-glutamate

anisole

docosanoyl chloride

docosanoic acid

thionyl chloride

→

dibenzyl N-(N-docosanoyl-L-valyl)-L-glutamate

수율 47.3%

용매

triethylamine

trifluoroacetic acid

tetrahydrofuran

benzene

benzene

tetrahydrofuran

반응 조건

후처리

1. 1
   온도was refluxed for 1 hour
2. 2
   기타After removal of the solvent under reduced pressure
3. 3
   기타benzene was evaporated off
4. 4
   기타to give crude docosanoyl chloride
5. 5
   기타Evaporation of trifluoroacetic acid under reduced pressure
6. 6
   기타gave a residue which
7. 7
   workup.DISTILLATIONBenzene was distilled off
8. 8
   기타to leave crude dibenzyl N-(L-valyl)-L-glutamate, which
9. 9
   기타the solvent was removed under reduced pressure
10. 10
    workup.DISSOLUTIONthe residue was dissolved in chloroform
11. 11
    세척The chloroform solution was washed with 1N sodium hydroxide solution, 1N hydrochloric acid solution
12. 12
    건조an aqueous solution of sodium bicarbonate successively, and then dried over magnesium sulfate
13. 13
    기타After evaporation of the solvent
14. 14
    기타the residue was purified
15. 15
    세척Elution with chloroform

실험 절차

A mixture of docosanoic acid (500 mg) and thionyl chloride (2 ml) in benzene (5 ml) was refluxed for 1 hour. After removal of the solvent under reduced pressure, the residue was taken up in benzene and benzene was evaporated off. This operation was repeated three times to give crude docosanoyl chloride. Meanwhile, a solution of dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)-L-glutamate (773 mg) and anisole (0.25 ml) in trifluoroacetic acid (1 ml) was stirred at 0° C. for 1 hour. Evaporation of trifluoroacetic acid under reduced pressure gave a residue which was taken up in benzene. Benzene was distilled off by using a high vacuum pump. This operation was repeated three times to leave crude dibenzyl N-(L-valyl)-L-glutamate, which was dissolved in tetrahydrofuran (5 ml). To this solution were added triethylamine (0.7 ml) and a solution of docosanoyl chloride prepared as mentioned above in tetrahydrofuran (3 ml). After the resulting mixture was stirred at room temperature for 3 hours, the solvent was removed under reduced pressure, and the residue was dissolved in chloroform. The chloroform solution was washed with 1N sodium hydroxide solution, 1N hydrochloric acid solution, and an aqueous solution of sodium bicarbonate successively, and then dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by being subjected to a silica gel column chromatography. Elution with chloroform and an usual work-up afforded dibenzyl N-(N-docosanoyl-L-valyl)-L-glutamate (520 mg, powder).

출처