Sodium Hydroxide → [7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid

Participants

Reaction Steps

A solution of ethyl [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetate (Preparation 46) (77 mg, 0.164 mmol) in methanol (30 ml) was stirred at room temp and sodium hydroxide (3 ml, 6.00 mmol) added. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo, the solid was triturated with methanol (˜5 ml) and the resultant solid filtered off and dried. The solid was suspended in methanol (˜30 ml) and acetic acid added to take the pH of the solution to 5-6, the solvent was removed in vacuo. The resultant residue was dissolved in DCM (˜30 ml) and water (˜30 ml) and the layers partitioned. The aqueous was re-extracted with DCM (˜20 ml) and the combined organics were passed through a phase separation cartridge and the solvent reduced in vacuo. The resultant residue was dried in a drying pistol at 60° C. to yield the title compound (22 mg, 0.047 mmol, 29% yield) as an off white solid. δH (d6DMSO, 400 MHz): 8.19 (1H, s), 8.11 (1H, d), 7.82-7.90 (2H, m), 7.44 (1H, d), 7.36 (1H, d), 4.89 (1H, sept), 3.34 (2H, s), 3.07-2.98 (4H, m), 2.91-2.86 (4H, m), 1.37 (6H, d. MS (ES+): C23H2435ClN3O4 requires 441; found 442 [M+H]+.

Provenance & Evidence