Ammonium Acetate → HCID 58979133, compound

Participants

Reaction Steps

A mixture of biphenyl-4-carboxylic acid 2-amino-3-methoxycarbonyl-1-methyl-allyl ester (566 g, 1.74 mol, 1 eq) and ammonium acetate (283 g, 3.67 mol) in glacial acetic acid (11.3 L) was heated at reflux for 2 h, cooled, and concentrated. The residue was coevaporated with toluene (2×2.5 L) and EtOAc (2.5 L). The mixture was diluted with EtOAc (6.6 L) and transferred with EtOAc (2.2 L) to a bottom outlet separation flask. The mixture was washed twice with water (2.2 L), saturated aqueous NaHCO3 (1.1 L), and brine (2×2.2 L). The organic layer was dried (Na2SO4, 550 g), filtered with the aid of EtOAc (1.1 L), and concentrated. The residue was dissolved in isopropanol (2 L) at 50° C. and allowed to cool overnight at room temperature. The mixture was kept at 0° C. to 5° C. for 1 h. The precipitated solid was broken up and collected by filtration. The solid was washed with cold isopropanol (4×0.55 L) and dried overnight in a vacuum oven at 50° C. to yield 428 g of the title compound (72% from Step 2).

Provenance & Evidence