반응 #2458998

반응 방정식

(Z)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]acrylamide

trifluoroacetic acid

triethylsilane

→

(Z)-3 [(2S,4S)-N-allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]acrylamide

용매

methylene chloride

반응 조건

후처리

1. 1
   온도cooling under nitrogen
2. 2
   농축concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with methylene chloride (5 ml)
4. 4
   농축The mixture was concentrated again
5. 5
   추출extracted with ethyl acetate (50 ml)
6. 6
   세척The organic layer was washed with 0.1M phosphate buffer (pH 5.7×2) and saturated aqueous sodium chloride
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축concentrated

실험 절차

To a solution of (Z)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]acrylamide (1.02 g, 2.06 mmol) in methylene chloride (1 ml) were added trifluoroacetic acid (1 ml) and triethylsilane (0.33 ml, 2.07 mmol) under ice-cooling under nitrogen. The reaction mixture was stirred for 30 minutes at the same temperature, concentrated under reduced pressure, and diluted with methylene chloride (5 ml). The mixture was concentrated again, and extracted with ethyl acetate (50 ml). The organic layer was washed with 0.1M phosphate buffer (pH 5.7×2) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated to give (Z)-3 [(2S,4S)-N-allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]acrylamide, which was used for the next reaction without purification. ##STR328##

출처