Triethylamine → (-)-N-Acetylphenylalanine

HRID 2099920Notes

Reaction equation

HRID 2099920 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].[H][H]>CO>[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

5

Reactant 3

HCID 8471TriethylamineHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 101184(-)-N-Acetylphenylalanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

The atmosphere in a 25 mL-recovery flask was substituted with nitrogen, and 3 mL of deoxygenized methanol and triethylamine (20.9 μL, 0.15 mmol) were added to the flask as the reaction solvent. α-Acetamidocinnamic acid (0.20 g, 0.98 mmol) and [Rh(CLPL-S)(COD)]BF4 (3.95 mg, 0.0049 mmol) were weighed in a 50 mL-Pyrex (registered trade name) test tube for autoclaving, the tube was put into an autoclave together with a stirrer in the tube, and the atmosphere in the autoclave was substituted with nitrogen. The reaction solvent in a volume of 2 mL was added to the mixture, the atmosphere in the autoclave was sufficiently substituted with hydrogen, and then pressurized with 2 MPa of hydrogen, and the reaction mixture was stirred at 40° C. for 22 hours. After 22 hours, the atmosphere in the autoclave was returned to ordinary pressure, and the reaction mixture was concentrated in an evaporator. The concentrated residue was added with 5 mL of 2 M aqueous sodium hydroxide for dissolution, and the solution was washed with 5 mL of ethyl acetate. The aqueous layer was separated, and added with diluted hydrochloric acid until pH of the aqueous layer became lower than 2, and the produced oil was extracted with 10 mL of ethyl acetate. The organic layer was concentrated in an evaporator to obtain (R)-N-acetylphenylalanine quantitatively.

Workup

  1. additionwere added to the flask as the reaction solvent
  2. customthe tube was put into an autoclave together with a stirrer in the tube
  3. additionThe reaction solvent in a volume of 2 mL was added to the mixture
  4. waitAfter 22 hours
  5. concentrationthe reaction mixture was concentrated in an evaporator
  6. additionThe concentrated residue was added with 5 mL of 2 M aqueous sodium hydroxide for dissolution
  7. washthe solution was washed with 5 mL of ethyl acetate
  8. customThe aqueous layer was separated
  9. additionadded with diluted hydrochloric acid until pH of the aqueous layer
  10. extractionthe produced oil was extracted with 10 mL of ethyl acetate
  11. concentrationThe organic layer was concentrated in an evaporator

Sources & evidence

ORD record
ord-726199dfa4234070ad873f57f47fa292
Source dataset
uspto-grants-2009_08
Patent number
US07569730B2

Reaction notes

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