反応 #72928

反応方程式

2-phenyl-D-alanine

trimethylammonium hydroxide

diterbutylcarbonate

→

title product

N-(tert-butoxycarbonyl)-2-phenyl-D-alanine

溶媒

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The solvent was then removed under vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in water
4. 4
   洗浄washed with diethylether
5. 5
   抽出the product was extracted with ethyl acetate (3×20 mL)
6. 6
   洗浄The combined organic phase was washed with water
7. 7
   乾燥dried over Na2SO4
8. 8
   その他evaporated

実験手順

To a suspension of 500 mg of 2-phenyl-D-alanine (3.02 mmol) and trimethylammonium hydroxide (aqueous solution 10%, 2.8 mL, 3.02 mmol) in 15 mL of acetonitrile, diterbutylcarbonate (1.047 g, 4.8 mmol) was added and the mixture was stirred at room temperature for 2 days. The solvent was then removed under vacuo, the residue was dissolved in water and washed with diethylether. The aqueous layer was acidified to pH=3-4 with citric acid and the product was extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with water, dried over Na2SO4 and evaporated. The title product was recovered as white solid (630 mg, yield 78%).

出典