Chloroacetone → HCID 57642030, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of [(S)-1-carbamoyl-2-(4-hydroxyphenyl)ethyl]-carbamic acid tert-butyl ester (3.00 g, 10.7 mmol) and potassium carbonate (7.40 g, 53.5 mmol) in N,N-dimethylformamide (50 ml) were added subsequently chloroacetone (1.02 ml, 12.8 mmol) and tetrabutylammonium iodide (197 mg, 0.54 mmol). The reaction mixture was heated to 90° C. for 16 h and cooled to room temperature. It was diluted with water (100 ml) and acidified with a 10% solution of sodium hydrogensulphate to pH 2. Ethyl acetate (300 ml) was added. The phases were separated. The organic layer was washed with water (3×150 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to give 2.65 g of {(S)-1-carbamoyl-2-[4-(2-oxopropoxy)phenyl]ethyl}carbamic acid tert-butyl ester.

Provenance & Evidence