Sodium Carbonate → HCID 68158136, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-fluoro-2-phenylaminoaniline (3.0 g, 14.85 mmol), tert-butoxycarbonyl glycine (2.4 g, 15 mmol) and HOAt (0.68 g, 5 mmol) in DCM (20 mL) and DMF (1 mL) at 0° C. was added EDCI (2.88 g, 15 mmol). The mixture was stirred at 0° C. for 1 h. To the reaction mixture was added a saturated aqueous solution of NaHCO3 (20 mL), saturated aqueous solution of Na2CO3 (10 mL) and water (10 mL). The mixture was extracted with DCM (2×20 mL) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM) to afford the title compound as a brown gum, (4.79 g, 89%). 1H NMR δ (ppm) (CHCl3-d): 7.95 (1H, s), 7.50 (1H, dd, J=8.83, 5.91 Hz), 7.32-7.22 (2H, m), 6.98-6.97 (4H, m), 6.68 (1H, dt, J=8.6, 2.7 Hz), 6.05 (1H, s), 5.06 (1H, s), 3.89 (2H, d, J=5.92 Hz), 1.42 (9H, s)

Provenance & Evidence