Ammonium Chloride → HCID 68833154, compound

Participants

Reaction Steps

Di-iso-propylethylamine (2.08 g, 2.80 mL, 16.0 mmol) was added in one portion to a stirred suspension of 4-(benzyloxy)-3-(4-bromophenyl)-4-oxobutanoic acid (1.45 g, 4.01 mmol), ammonium chloride (0.214 g, 4.01 mmol) and N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (1.68 g, 4.41 mmol) in dimethylformamide (20 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 (10% methanol: dichloromethane) to give the title compound as a white solid (1.23 g, 85%). LC/MS: 3.14 min; z/e 362 and 364, calcd (M+1) 362 and 364. 1H NMR (400 MHz: DMSO-d6): 7.55 (2H), 7.30 (8H), 6.85 (1H), 5.05 (2H), 4.05 (1H), 2.90 (1H), 2.50 (1H).

Provenance & Evidence