Triethylamine → (-)-N-Acetylphenylalanine

Participants

Reaction Conditions

Reaction Steps

0.0025 m-mol of rhodium-1,5-cyclooctadienechloride complex, 0.0065 m-mol of one of the asymmetric ligand compounds indicated in Table 1 and 0.25 m-mol of triethylamine were dissolved in 20 ml of ethanol, and 5 m-mol of α-acetamidocinnamic acid was added to the solution. The mixture was stirred for 20 hours at 50° C. and under a hydrogen atmosphere of 20 atm. The reaction mixture was concentrated under reduced pressure and then dissolved in 0.5N aqueous solution of caustic soda. Insolubles were filtered off and the filtrate was made acid with diluted hydrochloric acid and extracted with ether. The organic layer was washed with water and dried. The solvent was distilled off to obtain optically active (R)-N-acetylphenylalanine. The results of Synthesis Nos. 1-5 are shown in Table 1.

Provenance & Evidence