Hydrochloric Acid → N-Acetyl-L-phenylalanine

HRID 1292538Notes

Reaction equation

HRID 1292538 reaction equation
[NH2:1][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:13](OC(=O)C)(=[O:15])[CH3:14].Cl>C(=O)([O-])O.[Na+]>[C:13]([NH:1][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)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 7918Acetic Anhydride

Product 1

HCID 74839N-Acetyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

After 4.96 g of L-phenylalanine was dissolved in 5% sodium hydrogencarbonate aqueous solution, 3.4 ml of acetic anhydride was dropwise added to the solution over an hour under ice cooling. After completion of the dropwise addition, the mixture was stirred for 2 hours at room temperature. Then 17 ml of hydrochloric acid was added to the reaction mixture to render the system acidic. The precipitated white solid was extracted once with 100 ml of ethyl acetate and twice with 40 ml each of the same solvent. The oily layer was dried over anhydrous sodium sulfate and the solvent was distilled off to give 5.61 g of N-acetyl-L-phenylalanine as white crystalline powders. Yield, 90.3%.

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionThe precipitated white solid was extracted once with 100 ml of ethyl acetate and twice with 40 ml each of the same solvent
  3. dry with materialThe oily layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-aa517b6c32c142df8d91a43eb90ea7b7
Source dataset
uspto-grants-1998_05
Patent number
US05756763

Reaction notes

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