반응 #1771998

반응 방정식

ethylacetate

Fmoc-norValinol

triethylamine

→

9-Fluorenylmethoxycarbonyl-norvalinal

용매

—

hexanes

dimethylsulfoxide

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the chilled solution
2. 2
   기타the completion of the reaction
3. 3
   기타The dichloromethane was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe remaining residue was dissolved in ethylacetate
5. 5
   세척washed with water (2×50 ml), 1N saturated sodium bisulfate (2×50 ml), saturated sodium bicarbonate (2×50 ml) and brine (50 ml)
6. 6
   농축The organic layer was concentrated
7. 7
   기타to yield a white solid
8. 8
   기타Theoretical yield (21.57 g)
9. 9
   기타the reaction was taken to the next step without further purification

실험 절차

To a solution of Fmoc-norValinol (21.70 g, 66.77 mmol) in dichloromethane (668 ml) was added triethylamine (37.23 ml, 267 mmol) and the solution was cooled to 0° C. A suspension of pyridine sulfur trioxide complex (42.51 g, 267 mmol) in dimethylsulfoxide (96 ml) was added to the chilled solution. After one hour, TLC in 2:3 ethylacetate:hexanes confirmed the completion of the reaction. The dichloromethane was removed under reduced pressure and the remaining residue was dissolved in ethylacetate and washed with water (2×50 ml), 1N saturated sodium bisulfate (2×50 ml), saturated sodium bicarbonate (2×50 ml) and brine (50 ml). The organic layer was concentrated to yield a white solid. Theoretical yield (21.57 g) was assumed and the reaction was taken to the next step without further purification.

출처