Hydrochloric Acid → HCID 67103622, compound

Participants

Reaction Steps

A stirred solution of methyl 3-methyl-2-oxo-4-imidazolidinecarboxylate (316 mg, 2 mmol) (prepared as described in step (ii) of Example 8) in N,N-dimethylformamide (5 ml) was cooled to 0° C. under argon and treated with sodium hydride (60% dispersion in oil) (120 mg, 3.00 mmol). After 10 minutes 2-iodopropane (0.400 ml, 4.00 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours. A solution of lithium hydroxide (57.5 mg, 2.400 mmol) in water (1 ml) was added and the reaction mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (2M) was added to adjust the pH of the mixture to pH 2 and the solvent was evaporated. Dimethylsulfoxide (3 ml) was added to the residue and the suspension was filtered. The filtrate was purified by mass-directed automated HPLC to give 3-methyl-1-(1-methylethyl)-2-oxo-4-imidazolidinecarboxylic acid (100 mg, 27%, over 2 steps). LC/MS [M+H]+=187.

Provenance & Evidence