Sodium Hydroxide → HCID 71239510, compound

Participants

Reaction Steps

To a mixture of 3-{4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]-benzoylamino}-propionic acid methyl ester (44 mg, 0.1 mM) in 1:1 mixture of THF/MeOH (1 mL) was added 1N NaOH solution (0.25 mL, 0.25 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 (˜100%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.93 (d, J=6.59 Hz, 3 H) 0.98 (d, J=6.34 Hz, 3 H) 1.56 (dt, J=13.30, 6.77 Hz, 1 H) 1.71 (dt, J=13.36, 6.62 Hz, 1 H) 1.76-1.85 (m, 1 H) 2.46 (t, J=7.07 Hz, 2 H) 2.59 (s, 3 H) 3.36-3.46 (m, 2 H) 4.64 (t, J=7.07 Hz, 1 H) 7.10 (br. s., 1 H) 7.21 (br. s., 1 H) 7.26 (d, J=6.83 Hz, 1 H) 7.32 (t, J=7.56 Hz, 1 H) 7.45 (d, J=8.05 Hz, 1 H) 7.53 (d, J=8.05 Hz, 2 H) 7.76 (d, J=8.29 Hz, 2 H) 8.42 (t, J=5.49 Hz, 1 H) 8.60 (d, J=2.44 Hz, 1 H), one proton was exchanged. LC-MS: 420.2 (M+1).

Provenance & Evidence