Triethylamine → Capravirine

Participants

Reaction Conditions

Reaction Steps

The compound (13) (250 mg, 0.91 mmol) was dissolved in N,N-dimethylformamide (4 ml). The solution was cooled down to −30° C. under nitrogen atmosphere. To the solution were added, alternately each four time, a solution of the compound (3) (77 mg, 0.36 mmol) in toluene (150 mg) and a solution of triethylamine (36 mg, 0.36 mg) in toluene (150 mg), and additionally added a solution of the compound (3) (77 mg, 0.36 mmol) in toluene (150 mg). The reaction mixture was stirred at −30° C. for 30 minutes, and ethyl acetate and aqueous sodium hydrogen carbonate were added thereto. The objective (14) was extracted into the ethyl acetate layer. Diluted aqueous hydrochloric acid was added to the ethyl acetate layer to transfer the objective compound into the aqueous layer. The aqueous solution was neutralized by aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give oily residue. The oily residue was dissolved in methanol (0.9 ml), and water (0.7 ml) was added dropwise thereto for 1–2 minutes at room temperature for crystallization. The suspension was stirred for 30 minutes at room temperature, additionally for 30 minutes under ice-cooling, filtered, washed with 50% aqueous methanol, and dried to yield the objective (14) (250 mg) as a white crystal. Yield 61%.

Provenance & Evidence