Pyridine → HCID 16124726, compound

Participants

Reaction Steps

(4-Adamantan-1-yl-phenoxy)-acetic acid (143.2 mg, 0.5-mmol) was dissolved in THF (5 mL), and oxalyl chloride (178.5 mg, 0.11 mL, 1.5 mmol) and one drop of DMF were added to the solution. After the mixture was stirred for 1 h at room temperature, 3-amino-4-hydroxy-benzoic acid methyl ester (125.4 mg, 0.75 mmol) and pyridine (0.05 mL) were added, and the resulting. Solution was stirred at room temperature overnight, and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4-anh), and concentrated. The residue was purified by (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester as a white solid (183.2 mg, 84.1% yield).

Provenance & Evidence