Tert-butoxycarbonylalanine → HCID 68157069, compound

Participants

Reaction Steps

N-(tert-Butoxycarbonyl)-L-alanine (150 mg, 0.78 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (165 mg, 0.86 mmol) and HOAt (106 mg, 0.78 mmol) were added to 4-fluoro-N2-pyrazin-2-yl-benzene-1,2-diamine (160 mg, 0.78 mmol) in DCM (10.0 ml) and DMF (1.00 ml) at 0° C. The reaction was stirred for 3 h then poured into water and the aqueous layer extracted with DCM (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% methanol/DCM) to yield the title compound (144 mg, 0.38 mmol, 50%). LCMS: RT 3.02 min [M+H]+ 376.2. 1H NMR (CDCl3, 400 MHz): δ 8.36 (1H, s), 8.12 (1H, dd, J2.8, 1.5 Hz), 8.03 (1H, br s), 8.02 (1H, d, J=2.7 Hz), 7.92 (1H, br s), 7.62 (1H, br s), 7.28 (1H, m), 6.77 (1H, td, J 8.4, 2.9 Hz), 4.97 (1H, br s), 4.20 (1H, m), 1.49 (3H, d, J 7.2 Hz), 1.45 (9H, s).

Provenance & Evidence