Dimethylformamide → HCID 10008274, compound

Participants

Reaction Steps

To a solution of the intermediate from step E (1.07 g, 2.13 mmol) in DMF (20 mL) was added 1-hydroxy-7-azabenzo-triazole (435 mg, 3.19 mmol), N,N-diisopropylethyl amine (557 μL, 3.19 mmol) β-alanine-t-butyl ester hydrochloride (465 mg, 2.55 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (489 mg, 2.55 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with EtOAc (150 mL), washed with 1N HCl, saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The yellow foam obtained was purified by flash chromatography using 2:5 ethylacetate-hexanes to give the title compound as a white solid. 1H NMR (CDCl3, 500 MHz): δ 7.75 (d, J=1.6 Hz, 2H), 7.73 (d, J=8.2 Hz, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.31 (t, J=1.6 Hz, 1H), 7.18 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.92 (t, J=5.7 Hz, 1H), 6.65 (s, 1H), 5.39 (s, 2H), 3.7 (q, J=5.9 Hz, 2H), 2.57 (t, J=6.1 Hz, 2H), 1.47 (s, 9H). LC-MS: 2.95 min; (M-56)=572.1.

Provenance & Evidence