L-Alaninol → HCID 58188282, compound

Participants

Reaction Steps

To a mixture of 5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (0.60 g, 2.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (470 mg, 2.4 mmol), 1-hydroxybenzotriazole hydrate (340 mg, 2.2 mmol), and CH2Cl2 (5 mL) were added (S)-2-aminopropan-1-ol (180 mg, 2.4 mmol) and N,N-diisopropylethylamine (0.58 mL, 3.3 mmol). The mixture was stirred at room temperature overnight, and then diluted with EtOAc, washed with aq. NaHCO3, brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-80% EtOAc/hexane) to yield a white solid. LC-MS: 328.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6): δ 8.48 (d, 1H, J=8.0 Hz), 8.40 (t, 1H, J=1.6 Hz), 8.37 (t, 1H, J=1.6 Hz), 8.28 (t, 1H, J=1.6 Hz), 7.69 (d, 2H, J=8.0 Hz), 7.34 (d, 2H, J=8.0 Hz), 4.78 (t, 1H, J=5.6 Hz), 4.07 (m, 1H), 3.92 (s, 3H), 3.49 (m, 1H), 3.38 (m, 1H), 2.37 (s, 3H), 1.16 (d, 3H, J=6.8 Hz).

Provenance & Evidence