N-Methylpiperidine → N1-[1(5-fluoro-2-benzofuranyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide

4.7 g of N-methylpiperidine was added to a solution containing 9.7 g of N-isopropoxycarbonyl-L-valine dissolved in 100 ml of dichloromethane, at -20° C. and the mixture was stirred for 15 minutes at the same temperature. Subsequently, 6.5 g of isobutyl chloroformate was added to the mixture at -30° C. and then the whole mixture was stirred between -30° C. and -20° C. for 30 minutes. 8.5 g of 1-(5-fluoro-2-benzofuranyl)ethylamine was then added to the mixture at -50° C. The mixture was allowed to sit and warm naturally to room temperature and then stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the dichloromethane layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue, which was a crude crystal, was purified by column chromatography on silica gel, thus obtaining 10.6 g of the desired product in the form of a white powder.

1. stirringthe whole mixture was stirred between -30° C. and -20° C. for 30 minutes
2. stirringstirred for 15 hours at room temperature
3. washAfter the dichloromethane layer was washed with water
4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated
6. customwas purified by column chromatography on silica gel

ORD record

ord-8aecd91b16334c7d8781d0456268c90f

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05348976