Hydrochloric Acid → HCID 9855841, compound

Participants

Reaction Steps

(2R)-2-Propyl-4-hexynoic acid (2.0 g, 13 mmol, prepared according to U.S. Pat. No. 5,786,380) in dichloromethane (20 mL) was treated with 2 drops of N,N-dimethylformamide and freshly distilled oxalyl chloride (1.25 equivalents) at 0° C. The mixture was allowed to warm to ambient temperature. After stirring for 3 hours at ambient temperature, the solvents were removed under reduced pressure to provide crude acid chloride. The crude acid chloride was dissolved in dichloromethane (15 mL) and added dropwise to a solution of 2-aminoacetamide hydrochloride (14 mmol) and triethylamine (3.5 mL) in water at 0° C. The mixture was allowed to warm to ambient temperature. After stirring for 3 hours at ambient temperature, the mixture was cooled to about 5° C. and treated with 1N HCl until pH=2. The resulting white solid was collected by filtration, dried and recrystallized from ethyl acetate to provide the title compound (70% yield).

Provenance & Evidence