Hydrochloric Acid → HCID 46926794, compound

Participants

Reaction Steps

A 1 N aqueous solution of sodium hydroxide (2.0 mL) was added to a solution of methyl 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoate B-16 (94.0 mg, 0.20 mmol) in a 1:1 mixture of tetrahydrofuran:methanol (5.0 mL) at room temperature. After 12 h of stirring, the aqueous layer was acidified to pH 0 with a 1 N aqueous hydrogen chloride solution and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid) to give 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoic acid B-17 (54.7 mg, Yield=60%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.17 (s, 6H), 2.75 (s, 3H), 4.30 (s, 2H), 6.93 (d, J=8.5 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.41 (t, J=9.5 Hz, 1H), 7.64 (s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.97 (d, J=9.0 Hz, 1H), 8.16 (d, J=8.5 Hz, 1H), 8.21 (d, J=8.5 Hz, 1H), 8.29 (s, 1H), 8.51 (s, 2H), 8.67 (m, 1H), 10.86 (s, 1H); MS (ESI) [M+1]+ 456.

Provenance & Evidence