Sodium Hydroxide → HCID 71239279, compound

Participants

Reaction Steps

To a mixture of 3-{4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]-benzoylamino}-propionic acid methyl ester (12) (49 mg, 0.11 mM) in 1:1 mixture of THF/MeOH (1 mL) was added 1N NaOH solution (0.283 mL, 0.283 mM). The reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated to remove organic solvent. The aqueous solution was diluted with DCM (5 mL), acidified by 1N HCl solution to pH=3-4. The organic solution was separated and the aqueous solution was extracted with 10% i-PrOH-DCM (3×5 mL). The combined organic solution were dried (Na2SO4) and concentrated to give a yellow solid product (˜78%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.93 (d, J=6.59 Hz, 3H) 0.98 (d, J=6.59 Hz, 3 H) 1.53-1.60 (m, 1 H) 1.70 (dt, J=13.72, 6.68 Hz, 1 H) 1.76-1.83 (m, 1 H) 2.43 (s, 3 H) 2.47 (t, J=7.07 Hz, 2 H) 3.35-3.46 (m, 2 H) 4.65 (t, 1 H) 7.23 (br. s., 1 H) 7.37 (d, J=8.54 Hz, 1 H) 7.41 (br. s., 1 H) 7.54 (d, J=8.29 Hz, 2 H) 7.59-7.67 (m, 2 H) 7.76 (d, J=8.29 Hz, 2 H) 8.43 (t, J=5.49 Hz, 1 H) 8.61 (d, J=2.68 Hz, 1 H), one proton was exchanged. LC-MS: m/z 420.2 (M+1).

Provenance & Evidence