Sodium Hydroxide → 3-(4-{[3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-(4-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)propanoate (D141) (0.63 g, 1.133 mmol) in Isopropanol (5 mL) and Water (5.00 mL) was added NaOH (2.266 mL, 1.133 mmol). The reaction solution was heated to 90° C. for 1 hour. The solvent was evaporated in vacuo and the residue was acidified to pH=2-3, extracted with ethyl acetate, washed with water, dried and purified by Mass Directed AutoPrep to afford 3-(4-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-1-piperidinyl)propanoic acid (E106) (83 mg) as a TFA salt. δH (DMSO-d6, 400 MHz): 1.00 (3H, t), 1.28 (6H, d), 1.44 (2H, m), 1.72 (3H, m), 2.63 (4H, m), 2.83 (4H, m), 3.17 (4H, m), 4.79 (1H, m), 7.24 (2H, m), 7.32 (1H, d), 7.59 (1H, dd), 7.94 (1H, dd), 8.07 (1H, d). δF (DMSO-d6, 376 MHz): −73.5. MS (ES): C28H34ClN3O3S requires 527.2. found 528.1 (M+H+)

Provenance & Evidence