Hydrochloric Acid → Methyl N-acetyl-DL-phenylalaninate

HRID 1648995

Reaktionsgleichung

Reaktionsgleichung von HRID 1648995
[C:1]([N:4]([C:8](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:11])=[O:10])C(C)=O)(=[O:3])[CH3:2].[CH3:19][O-].[Na+].[H][H].Cl>[Ni].C(OCC)C.CO>[CH3:19][O:11][C:9](=[O:10])[CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:4][C:1](=[O:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 54405828HCID 54405828, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 97805Methyl N-acetyl-DL-phenylalaninateAusbeute 9.491,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A methanol (24 ml) slurry of the azlactone of N-acetyl-acetaminocinnamic acid (18.7 g, 0.10 mol) was treated with sodium methoxide (0.54 g. 0.01 mol) and the resulting dark solution was stirred for 10 minutes. The solution was then hydrogenated (200 psi hydrogen) over Raney nickel (5.87 g, 0.10 mol) in a sealed Parr autoclave at 50° C. for 2.5 hours. After cooling the reaction mixture was filtered through a Celite pad to remove the nickel, and concentrated in vacuo to afford a red oil which was slurried in diethyl ether (200 ml). The ethereal slurry was shaken with cold hydrochloric acid (0.5N, 100 ml) for approximately one minute. The layers were separated and the aqueous portion was extracted with additional diethyl ether (100 ml). The combined ether extract was washed with brine (100 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a reddish oily residue. The residue was titurated in petroleum ether (100 ml) and the solvent was evaporated to give 210 g (95%) N-acetyl-D,L-phenylalanine methyl ester as a light yellow solid which could be recrystallized from diethyl ether-petroleum ether to give a colorless solid. The melting point was 62°-63° C. The proton NMR agreed with the conclusion that N-acetyl-D,L-phenylalanine methyl ester was prepared.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. filtrationwas filtered through a Celite pad
  3. customto remove the nickel
  4. concentrationconcentrated in vacuo
  5. customto afford a red oil which
  6. customThe layers were separated
  7. extractionthe aqueous portion was extracted with additional diethyl ether (100 ml)
  8. extractionThe combined ether extract
  9. washwas washed with brine (100 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customto afford a reddish oily residue
  13. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-69f9cdd0aba9408ebf4b57415198c4f3
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04414404

Verknüpfte Notizen

Wird geladen…