Triethylamine → (-)-N-Acetylphenylalanine

Temperature

50 °C

0.005 m-mole of rhodium-dinorbornadieneperchlorate, 0.0065 m-mole of (2S,4S)-N-tert.-butoxycarbonyl-2-bis(3,5-dimethyl-4-methoxyphenyl)phosphinomethyl-4-bis(3,5-dimethyl-4-methoxyphenyl)phosphinopyrrolidine (Ii) and 0.25 m-mole 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 pressure 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. Conversion 100%; optical yield 98%.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutiondissolved in 0.5N aqueous solution of caustic soda
3. filtrationInsolubles were filtered off
4. extractionextracted with ether
5. washThe organic layer was washed with water
6. customdried
7. distillationThe solvent was distilled off

ORD record

ord-949921ea59b94a3d8743d5cecc5f47a3

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04985567