Sodium Hydroxide → HCID 44548735, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-β-alaninate (D78) (287 mg) in tetrahydrofuran (5 mL) and ethanol (5 mL) stirred at 20° C. was added a solution of sodium hydroxide (60 mg) in water (5 mL) in one charge. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was concentrated and then H2SO4 (0.1 M) solution was added dropwise until no further white precipitate was formed. The solid was filtered and recrystallized from EtOAc to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-β-alanine (E58) (130 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.28 (2H, t), 2.91 (2H, t), 3.68 (3H, s), 4.11 (2H, s), 4.88-4.91 (1H, m), 7.23 (1H, t), 7.45-7.50 (3H, m), 7.96 (1H, dd), 8.14 (1H, dd), 8.21 (1H, d). MS (ES): C24H26ClN4O4 requires 468. found 380.1 (M—NHC2H4COOH+).

Provenance & Evidence