Ammonia → 5-Nitrooxy-pentanoic acid amide

Temperature

0 °C

To a solution of compound 2 (1.30 g, 1.0 eq) in dry dichloromethane (20.0 mL) cooled to 0° C. was added triethylamine (1.30 mL, 1.2 eq) followed by ethyl chloroformate (0.83 mL, 1.1 eq). The reaction mixture was stirred at 0° C. for 45 minutes and 30% aqueous ammonia solution (15.0 mL) was added. The solution was stirred from 0° C. to RT for 18 hours and sodium sulphate was added to dry the mixture. The resulting mixture was filtered off and the filtrate was concentrated under vacuum. The residue was adsorbed on silica gel and purified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→98/2 (12CV*), 98/2 (6CV)] affording compound 3 as a white solid (1.10 g, yield=85%).

1. stirringThe solution was stirred from 0° C. to RT for 18 hours
2. customto dry the mixture
3. filtrationThe resulting mixture was filtered off
4. concentrationthe filtrate was concentrated under vacuum
5. custompurified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→98/2 (12CV*), 98/2 (6CV)]

ORD record

ord-e7921264d7424962a8d4bbd38a154f3e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365489B2