반응 #2018

반응 방정식

ethyl acetate

allyl alcohol

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

EDC

→

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

용매

—

hexanes

methylene chloride

반응 조건

후처리

1. 1
   기타the resulting homogeneous solution quenched with water
2. 2
   추출extracted with methylene chloride
3. 3
   세척The methylene chloride layer was washed with 5% aqueous citric acid
4. 4
   건조The methylene chloride layer was dried over anhydrous magnesium sulfate powder
5. 5
   여과filtered
6. 6
   기타evaporated under reduced pressure
7. 7
   기타to give an oil
8. 8
   기타afforded the product (408 mg; 60%) as a pale yellow gum

실험 절차

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).

출처