Sodium Hydroxide → (-)-(3-Isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetic acid

Participants

Reaction Steps

To a stirred solution of methyl (3-isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetate, isomer B from Step B (700 mg, 2.3 mmol) in MeOH (20 mL) was added 1 N aqueous NaOH (5.0 mL, 5.0 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction was quenched by addition of 1 N HCl (5 mL) and the reaction was poured into water (100 mL) and the mixture was adjusted to pH 3 with 1 N HCl. The aqueous mixture was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound. MS: m/z=291 (M+1).

Provenance & Evidence