Dimethylformamide → HCID 58420498, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing compound (6) (16.7 g, 41.6 mmol), compound (10) (5.58 g, 48.9 mmol), anhydrous DIEA (20.8 g, 161 mmol, dried over 4 Å sieves), and anhydrous DMF (128 mL) is heated at 70° C. under an atmosphere of argon gas. After heating for 6 h (LC-MS analysis shows ˜7% compound (6) remained), the reaction mixture is cooled to room temperature, diluted with EtOAc (500 mL), and washed with water (500 mL). The aqueous layer is extracted with EtOAc (500 mL), and the combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (500 mL). The organic layer is diluted with water (500 mL) and treated with an aqueous solution of HCl (4 N) until the aqueous layer is acidic (pH 2-3 after shaking the mixture vigorously). The organic layer is separated, and this process is repeated. The combined aqueous layers are diluted with EtOAc (500 mL) and treated with an aqueous solution of sodium hydroxide (6 N) until the aqueous layer is basic (pH ˜8 after shaking the mixture vigorously). The aqueous layer is separated, and this process is repeated. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving an orange solid. Crude solid is used directly to next reaction.

Provenance & Evidence