Ammonium Chloride → HCID 68833238, compound

Participants

Reaction Steps

Di-iso-propylethylamine (3.21 g, 4.33 mL, 24.8 mmol) was added in one portion to a stirred suspension of 4-(benzyloxy)-2-(4-bromophenyl)-4-oxobutanoic acid (2.25 g, 6.21 mmol), ammonium chloride (0.332 g, 6.21 mmol) and N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (2.36 g, 6.21 mmol) in dimethylformamide (40 mL) at room temperature under nitrogen. After stirring for 2 h the volatiles were evaporated and the residue partitioned between dichloromethane (50 mL) and aqueous hydrochloric acid solution (1.0 M; 50 mL). The phases were separated and the aqueous layer washed with dichloromethane (2×50 mL). The organic phases were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (5% methanol: dichloromethane) to give the title compound as a white solid (1.14 g, 51%). LC/MS: 3.20 min; z/e 362 and 364, calcd (M+1) 362 and 364. 1H NMR (400 MHz: CDCl3): 7.45 (2H), 7.30 (5H), 7.15 (2H), 5.45 (2H), 5.10 (2H), 3.95 (1H), 3.30 (1H), 2.70 (1H).

Provenance & Evidence