Hydrochloric Acid → HCID 67103622, compound

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.

1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
2. customthe solvent was evaporated
3. additionDimethylsulfoxide (3 ml) was added to the residue
4. filtrationthe suspension was filtered
5. customThe filtrate was purified

ORD record

ord-ef3834bb573e42dd89a05bce81a4e128

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932282B2