Diisopropylethylamine → HCID 24772470, compound

Participants

Reaction Steps

To a solution of the product from example 43A (90 mg, 0.25 mmol) in N,N-dimethylformamide (0.5 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol), N,N diisopropylethylamine (0.3 mL, 1.7 mmol), and 3,3-difluoroazetidine hydrochloride (130 mg, 1 mmol). The mixture was stirred at room temperature for 18 hours, diluted with ethyl acetate (10 mL) and washed with water and brine. The organic extract was dried over MgSO4 and concentrated. Purification by chromatography (0 to 75% ethyl acetate in hexane gradient) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.28 (d, J=6.4 Hz, 3H) 1.63-2.06 (m, 11H) 2.18 (s, 2H) 4.35-4.71 (m, 4H) 4.81-5.00 (m, 2H) 5.29-5.42 (m, 1H) 11.12 (s, 1H). MS (DCI/NH3) m/z 439.1 (M+H)+.

Provenance & Evidence