반응 #1987354

반응 방정식

isobutyl chloroformate

N-methylpiperidine

2-(4-cyanophenoxy)-1-methylethylamine

N-phenoxycarbonyl-L-valine

→

desired product

수율 22.3%

N1 -[2-(4-cyanophenoxy)-1-methylethyl]-N2 -phenoxycarbonyl-L-valinamide

수율 22.3%

용매

methylene chloride

Water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the mixture at -40° C.
2. 2
   온도warm naturally to room temperature
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.STIRRINGstirred for 20 hours at room temperature
5. 5
   세척After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water
6. 6
   건조the organic layer was dried over anhydrous magnesium sulfate
7. 7
   기타the methylene chloride was removed under reduced pressure
8. 8
   기타was purified by column chromatography on silica gel

실험 절차

1.3 g of N-methylpiperidine was added to a solution containing 3 g of N-phenoxycarbonyl-L-valine dissolved in 50 mL of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature, 1.7 g of isobutyl chloroformate was added to the mixture at -40° C., and stirred for 1 hour at -20° C. 2.2 g of 2-(4-cyanophenoxy)-1-methylethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature, with stirring, and stirred for 20 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue, which was a crude crystal, was purified by column chromatography on silica gel, thus obtaining 1.1 g of the desired product in the form of a white powder (yield: 22%).

출처