N-Acetyl-L-phenylalanine → Acetyl-L-phenylalanine ethyl ester

HRID 2298748Notes

Reaction equation

HRID 2298748 reaction equation
[NH:1]([C:13]([CH3:15])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:16](O)(=O)[CH:17]=C.N(C(C)=O)[C@H](C(O)=O)CC1C=CC=CC=1>C(O)C.Cl>[NH:1]([C:13]([CH3:15])=[O:14])[C@H:2]([C:10]([O:12][CH2:16][CH3:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 74839N-Acetyl-L-phenylalanineHCID 131723716N-Ac-L-Phe acrylic acid

Product 1

HCID 94229Acetyl-L-phenylalanine ethyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

The synthesis of N-Ac-L-Phe-acrylic acid is shown below in Scheme B. To a solution of N-Ac-L-Phe (5.0 g, 24.1 mmol) in 120 ml of ethanol was added a few drops of concentrated HCl. The reaction mixture was refluxed overnight, then concentrated under reduced pressure. The residual solid was dissolved in ethyl acetate, washed twice with dilute NaHCO3, then once with water. The organic phase was dried over MgSO4, concentrated under reduced pressure, and dried under vacuum, to give N-Ac-Phe-OEt (7) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residual solid was dissolved in ethyl acetate
  4. washwashed twice with dilute NaHCO3
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customdried under vacuum

Sources & evidence

ORD record
ord-59719847348d4cbb9e45cf451071dc94
Source dataset
uspto-grants-2002_12
Patent number
US06495514B1

Reaction notes

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