反応 #586929

反応方程式

Glycine

9-fluorenylmethoxycarbonyl chloride

water

→

Fmoc-Gly

溶媒

—

NaCO3

dioxane

反応条件

後処理

1. 1
   その他To the resulting solution, which had been put into an ice bath
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 4 hours
3. 3
   その他The aqueous phase layer was separated from the reaction mixture
4. 4
   抽出followed by extraction with ethyl acetate three times (75 ml×3)
5. 5
   その他The organic phase layer was recovered
6. 6
   濃縮concentrated
7. 7
   その他to obtain crude product of 1.70 g
8. 8
   その他The crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid
9. 9
   その他was obtained
10. 10
    ろ過after filtration at a reduced pressure

実験手順

Glycine (Gly) (0.5 g, 6.66 mmole) was dissolved in 10% NaCO3 (14 ml) under stirring in a 50-ml flask. To the resulting solution, which had been put into an ice bath, 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) (1.72 g, 6.66 mmol) in dioxane (12 ml) was gradually added. The reaction mixture was stirred at room temperature for 4 hours, and water (150 ml) was then added. The aqueous phase layer was separated from the reaction mixture and stripped with ether three times (75 ml×3). The stripped aqueous layer was acidified with 2N HCl aqueous solution to a pH value of 2, followed by extraction with ethyl acetate three times (75 ml×3). The organic phase layer was recovered and concentrated to obtain crude product of 1.70 g. The crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid denoted as Fmoc-Gly was obtained after filtration at a reduced pressure. Yield: 1.69 g (85%).

出典