Pyridine → HCID 71008607, compound

Participants

Reaction Conditions

Reaction Steps

TFAA (73 μL, 0.522 mmol) is treated with CH2Cl2 (1.0 mL) and pyridine (42.2 μL, 0.522 mmol) and cooled to 0° C. To this mixture is added a solution of Example 147 (48.0 mg, 0.104 mmol) in CH2Cl2 (0.5 mL) and the resulting mixture is warmed to room temperature and stirred for 1 hour. The reaction is then quenched by the addition of saturated NaHCO3 and stirred for 30 minutes. The mixture is diluted with CH2Cl2 and water and the layers separated. The aqueous layer is extracted again with CH2Cl2 and the combined organics are dried over Na2SO4, filtered, and concentrated. The crude residue is then treated with THF (1.0 mL), water (0.5 mL), methanol (0.2 mL), and lithium hydroxide monohydrate (8.6 mg, 0.21 mmol) and the resulting mixture is heated at 40° C. for 30 minutes. The mixture is then diluted with saturated NaHCO3 and ethyl acetate and the layers separated. The aqueous is then extracted with ethyl acetate again and the combined organics are dried over Na2SO4, filtered, and concentrated. The resulting residue is triturated with acetonitrile to give the title compound (12.0 mg).

Provenance & Evidence