Hydrochloric Acid → HCID 14326862, compound

Participants

Reaction Steps

To a magnetically stirred suspension of 5.00 g (22.1 mmol) of diphenylpropionic acid in 25 ml of dry dichloromethane under nitrogen was added 2.12 ml (24.3 mmol) of oxalyl chloride followed by two drops of dimethylformamide. After stirring for one hour, the solution was rotary evaporated and the residue placed under high vacuum to further remove any remaining volatiles. The resulting yellow oil was added to a solution of 3.65 g (22.1 mmol) of racemic phenylalanine in 50 ml of saturated aqueous sodium bicarbonate and 10 ml of tetrahydrofuran. The mixture was allowed to stir for three hours while maintaining the pH at 8. The mixture was then acidified to pH 2 with concentrated hydrochloric acid and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with 10% aqueous hydrochloric acid, water, brine, dried over magnesium sulfate, filtered and rotary evaporated. Recrystallization of the residue from toluene gave 4.60 g of the title compound as an off-white solid, melting point 138°-140° C.

Provenance & Evidence