Compound 95
ethyl (S)-2-acetamido-3-(4-(azetidin-1-yl)phenyl)propanoate
From: Practical and regioselective amination of arenes using alkyl amines
View in PubChem | MDL Molfile | Chemdraw file
Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, azetidine hydrochloride (10 mg, 0.1 mmol), ethyl L-acetylphenylalaninate (47 mg, 0.2 mmol) and 6.0 equiv. of HClO4 gave 95 and 95* (29 mg, 98%) as an oil. p:m 3:1. Rf 0.15 [CHCl3–EtOH (95:5)]; FT-IR νmax (film)/cm–1 2936, 2883, 1786, 1717, 1292, 1259, 1084; 1H NMR (500 MHz, CDCl3) δ 6.92 (2H, d, J = 7.9 Hz), 6.36 (2H, d, J = 7.8 Hz), 5.87 (1H, d, J = 7.2 Hz), 4.78 (1H, q, J = 6.1 Hz), 4.17 (2H, q, J = 6.9, 6.5 Hz), 3.84 (4H, t, J = 7.0 Hz), 3.01 (2H, d, J = 5.5 Hz), 2.35 (2H, p, J = 7.1 Hz), 1.98 (3H, s), 1.26 (3H, t, J = 7.1 Hz); 13C NMR (126 MHz, CDCl3) δ 172.0, 169.6, 151.5, 129.9, 124.2, 111.6, 61.5, 53.5, 52.6, 37.2, 23.3, 17.1, 14.3; HRMS (ASAP POS): Found MH+ 291.1707, C16H23N2O3 requires 291.1703.
