反应详情

温度

80 °C

To a suspension of glycine ethyl ester hydrochloride (41.9 g, 0.3 mol) in ethanol (300 mL) was added triethylamine (41.8 mL, 0.3 mol) and ethyl acrylate (10.8 mL, 0.1 mol) in an ice bath, and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and water (400 mL) was added to the residue, and the mixture was extracted with ethyl acetate (200 mL×3). The extract was washed with water (200 mL×2) and saturated aqueous solution of sodium chloride (200 mL) in this order, an the dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was dissolved in acetone (150 mL). To this solution were added aqueous solution of sodium carbonate (11.5 g, 108 mmol) (50 mL) and a solution of benzyloxycarbonyl chloride (18.4 g, 108 mmol) in acetone (50 mL) in an ice bath, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and water (400 mL) was added to the residue. The mixture was extracted with ethyl acetate (200 mL×3), and the extract was washed with saturated aqueous solution of sodium chloride (200 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 5:1) to obtain 31.1 g (92%) of the title compound as a colorless oily product.

1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (400 mL)
2. additionwas added to the residue
3. extractionthe mixture was extracted with ethyl acetate (200 mL×3)
4. washThe extract was washed with water (200 mL×2) and saturated aqueous solution of sodium chloride (200 mL) in this order
5. dry with materialan the dried with anhydrous sodium sulfate
6. filtrationAfter the filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. dissolutionthe residue was dissolved in acetone (150 mL)
9. concentrationThe reaction mixture was concentrated under reduced pressure, and water (400 mL)
10. additionwas added to the residue
11. extractionThe mixture was extracted with ethyl acetate (200 mL×3)
12. washthe extract was washed with saturated aqueous solution of sodium chloride (200 mL)
13. dry with materialdried with anhydrous sodium sulfate
14. filtrationAfter the filtration
15. concentrationthe filtrate was concentrated under reduced pressure
16. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 5:1)