Potassium Carbonate → HCID 68430670, compound

Participants

Reaction Steps

Add one drop of dimethylformamide to a solution of 6-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridine-2-carboxylic acid (800 mg, 2.43 mmol) and oxalyl chloride (0.23 mL, 2.67 mmol) in dichloromethane (24 mL) (gas evolution), stir 1 hour. Add a solution of methyl 3-aminobenzoate (365 mg, 2.43 mmol) and potassium carbonate (671 mg, 4.86 mmol) in acetone (16 mL). Stir resultant mixture for 16 hours. Dilute with dichloromethane (100 mL) and 1N hydrochloric acid (100 mL). Extract aqueous phase with dichloromethane, wash combined organic phase with saturated sodium bicarbonate solution. Dry organic phase over sodium sulfate and condense under reduced pressure. Triturate the residue in 1:1 acetone/diethyl ether. Dissolve resultant solid in ethyl acetate and wash with saturated sodium bicarbonate (2×), Dry organic phase over sodium sulfate and condense under reduced pressure to afford the title compound as a white solid (856 mg, 1.85 mmol). MS (m/z): 463 (M+1).

Provenance & Evidence