N-Methylpiperidine → N1-[1-methyl-2-(4-trifluoromethylphenoxy)ethyl]-N2-phenoxycarbonyl-L-valinamide

Temperatur

-20 °C

1.6 g of N-methylpiperidine was added to a solution containing 4.0 g of N-phenoxycarbonyl-L-valine dissolved in 80 ml of methylene chloride, at -20° C. After the mixture was stirred for 15 minutes at the same temperature, 2.2 g of isobutyl chloroformate was added to the mixture, and stirred for 1 hour at -20° C. 3.5 g of 1-methyl-2-(4-trifluoromethylphenoxy)ethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and was 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 was purified by column chromatography on silica gel, thus obtaining 2.8 g of the desired product in the form of a white crystal (yield: 40%).

1. additionwas added to the mixture
2. temperaturewarm naturally to room temperature
3. stirringwhile being stirred
4. stirringwas stirred for 20 hours at room temperature
5. washAfter the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water
6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
7. customthe methylene chloride was removed under reduced pressure
8. customThe residue was purified by column chromatography on silica gel

ORD-Eintrag

ord-94cc139f9f9f478a8a4ace4bf7eb4904

Quelldatensatz

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05574064