2-Phenylpropionic acid, (-)- → (2R)-2-phenyl-N-[2-(4-pyridyl)-1,3-benzoxazol-5-yl]propanamide

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Reaction Steps

Similarly prepared as per compound 8 procedure, using starting materials (R)-2-phenylpropanoic acid and compound 4 (4-pyridine) to obtain title compound Q49 as white solid (78%). 1H NMR (CDCl3, 400 MHz) δ 1.59 (d, J=7.2 Hz, 3H), 3.76 (q, J=6.8 Hz, 1H), 7.21-7.29 (m, 1H), 7.32-7.41 (m, 6H), 7.90 (s, 1H), 7.97 (d, J=4.8 Hz, 3H), 8.74 (s, 2H); 13C NMR (CDCl3, 100 MHz) δ 18.9, 48.0, 110.8, 112.3, 119.8, 121.2, 127.7, 127.8, 129.2, 134.3, 135.6, 141.1, 142.1, 147.7, 150.7, 161.4, 172.9; ESI-HRMS for C21H18N3O2 (M+H)+ calcd. 344.1399. found 344.1393 (% ee 99, tR=11.29 min).

Provenance & Evidence