反应 #2018

反应方程式

ethyl acetate

allyl alcohol

N-(t-Butoxycarbonyl)-O-benzyl-D-serine

EDC

→

N-(t-Butoxycarbonyl)-O-Benzyl-D-Serine Allyl Ester

溶剂

—

hexanes

methylene chloride

反应条件

后处理

1. 1
   其他the resulting homogeneous solution quenched with water
2. 2
   萃取extracted with methylene chloride
3. 3
   洗涤The methylene chloride layer was washed with 5% aqueous citric acid
4. 4
   干燥The methylene chloride layer was dried over anhydrous magnesium sulfate powder
5. 5
   过滤filtered
6. 6
   其他evaporated under reduced pressure
7. 7
   其他to give an oil
8. 8
   其他afforded the product (408 mg; 60%) as a pale yellow gum

实验过程

N-(t-Butoxycarbonyl)-O-benzyl-D-serine (600 mg; 2.03 mmol) was dissolved in dry methylene chloride (5 ml), allyl alcohol (152 μl; 2.23 mmol) and DMAP (25 mg; 0.20 mmol) added and finally EDC (428.5 mg; 2.24 mmol) added to the acid. The reaction mixture was stirred at room temperature for 2.5 h and the resulting homogeneous solution quenched with water and extracted with methylene chloride. The methylene chloride layer was washed with 5% aqueous citric acid then 10% aqueous sodium carbonate solution. The methylene chloride layer was dried over anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure to give an oil. Chromatography of the oil using ethyl acetate and hexanes 1:2 v/v afforded the product (408 mg; 60%) as a pale yellow gum. FAB-MS:- Calculated for C36H33N5 335.1; found 336.1 (M+1).

来源