Water → HCID 66920851, compound

Participants

Reaction Steps

To a solution of Example 115 (63 mg, 0.2 mmol) and N,N-diisopropylamine (40 μL, 0.22 mmol) in 0.5 mL of anhydrous N,N-dimethylformamide, was added tert-butyl bromoacetate (40 μL, 0.3 mmol). The resulting mixture was stirred at room temperature overnight, after which water was added, and the precipitate filtered. The solid was dissolved in 1 mL of trifluoroacetic acid, then stirred at room temperature for an additional hour. The mixture was concentrated, and purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to give 35 mg (41%, 2 steps) of the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.1 Hz, 3H), 3.46 (s, 2H), 4.30 (d, J=6.1 Hz, 2H), 4.46 (q, J=7.3 Hz, 2H), 6.46 (d, J=8.5 Hz, 2H), 7.02 (d, J=8.3 Hz, 2H), 7.07 (s, 1H), 7.28 (bs, 2H), 8.76 (t, J=6.2 Hz, 1H). MS (ESI+) m/e=370 (M+H)+.

Provenance & Evidence