Tert-butoxycarbonylalanine → HCID 68158042, compound

Participants

Reaction Steps

N-(tert-Butoxycarbonyl)-L-alanine (199 mg, 1.05 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (222 mg, 1.15 mmol) and HOAt (143 mg, 1.05 mmol) were added to 4-fluoro-N2-pyrimidin-2-yl-benzene-1,2-diamine (215 mg, 1.05 mmol) in DCM (8.0 ml) and DMF (800 μl) at 0° C. The reaction was stirred for 2 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 (350 mg, 0.93 mmol, 89%). LCMS: RT 2.98 min [M+H]+ 376.1. 1H NMR (CDCl3, 300 MHz): δ 8.48 (1H, br s), 8.42 (2H, d, J=4.9 Hz), 7.69 (1H, br s), 7.50 (2H, m), 6.84 (1H, td, J 8.5, 2.9 Hz), 6.76 (1H, t, J=4.9 Hz), 5.01 (1H, br s), 4.28 (1H, qn, J=7.6 Hz), 1.44 (9H, s), 1.43 (3H, d, J=7.4 Hz).

Provenance & Evidence