反応 #1844

反応方程式

Na2CO3

9-fluorenylmethyl succinimidyl carbonate

Gly-Pro-Hyp

Gly-Pro-Hyp

→

Fmoc-Gly-Pro-Hyp

溶媒

dimethoxyethane

dimethoxyethane

Na2CO3 H2O

反応条件

後処理

1. 1
   その他stored at 4° C
2. 2
   ろ過The solution was filtered
3. 3
   workup.ADDITION360 mL H2O was added to the filtrate
4. 4
   抽出The aqueous layer was extracted with 300 mL of diethyl ether
5. 5
   その他reduced to half volume at 80° C. under reduced pressure
6. 6
   workup.WAITstored at 4° C. for 24 h
7. 7
   その他The aqueous layer was decanted from the oily precipitate
8. 8
   その他reduced to ~30 mL at 81° C. under reduced pressure
9. 9
   workup.WAITstored at 4° C. for 24 h
10. 10
    その他The aqueous layer was decanted from the oily precipitate
11. 11
    その他Both oily precipitates
12. 12
    workup.DISSOLUTIONwere dissolved in a total of 20 mL methanol
13. 13
    workup.ADDITION250 mL ethyl acetate was added
14. 14
    その他A white residue was recovered by evaporation at 73° C. for 1 h under reduced pressure

実験手順

Fmoc-Gly-Pro-Hyp was synthesized from Gly-Pro-Hyp as follows: 3.0 g Gly-Pro-Hyp (10.5 mmol) was dissolved in 54 mL Na2CO3 --H2O (1:9) and stored at 4° C. 4.05 g 9-fluorenylmethyl succinimidyl carbonate (12.0 mmol) was dissolved in 45 mL dimethoxyethane and stirred at 4° C. The aqueous Na2CO3 solution was added slowly to the dimethoxyethane solution, and the reaction proceeded for 2.5 h at 4° C. and 21 h at room temperature. The solution was filtered, and 360 mL H2O was added to the filtrate. The aqueous layer was extracted with 300 mL of diethyl ether, acidified to pH 2 with concentrated HCl, reduced to half volume at 80° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate, reduced to ~30 mL at 81° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate. Both oily precipitates were dissolved in a total of 20 mL methanol, then 250 mL ethyl acetate was added. A white residue was recovered by evaporation at 73° C. for 1 h under reduced pressure; yield 3.23 g (6.39 mmol, 60.6%). The identity of the product as Fmoc-Gly-Pro-Hyp and its homogeneity was verified by thin layer chromatography [chloroform-methanol-HOAc (95:20:3)], scanning UV spectroscopy, and Edman degradation sequence analysis.

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