Triethylamine → (-)-N-Acetylphenylalanine

HRID 704096Notes

Reaction equation

HRID 704096 reaction equation
C(N(CC)CC)C.[C:8]([NH:11][C:12](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:10])[CH3:9]>C(O)C>[C:8]([NH:11][C@@H:12]([C:13]([OH:15])=[O:14])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acid

Product 1

HCID 101184(-)-N-Acetylphenylalanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ce516d22f224b35aa73b8172d8e71e4
Source dataset
uspto-grants-1991_01
Patent number
US04985567

Reaction notes

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