Pyridine → Acetylphenylalanine methyl ester

HRID 1728335

Reaktionsgleichung

Reaktionsgleichung von HRID 1728335
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:21](=[O:23])[CH3:22]

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 75736Methyl L-phenylalaninate hydrochloride

Produkt 1

HCID 704002Acetylphenylalanine methyl esterAusbeute 83,3 %

Versuchsvorschrift

To a solution of 2.73 g of L-phenylalanine methyl ester hydrochloride (12.7 mmol) in 5.00 g of pyridine (63.2 mmol) is dropwise added 12.90 g of acetic anhydride (126.0 mmol) under ice cooling. The mixture is allowed to stand for 2 hours and concentrated in vacuo. The residue is extracted with ethyl acetate. The extract is washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine in order, dried over sodium sulfate, filtered and concentrated in vacuo to give 2.34 g of the objective N-acetylphenylalanine methyl ester 4. Yield, 83.6%.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionThe residue is extracted with ethyl acetate
  3. washThe extract is washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine in order
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ce600d5419d406eb85eddbc8f83dfe6
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326780

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