Malonic Acid → 3-Amino-3-(4-fluorophenyl)propanoic acid

HRID 916175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916175
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:13])(=[O:12])[CH3:11].[NH4+:14].C(O)(=O)CC(O)=O>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH2:11][C:10]([OH:13])=[O:12])[NH2:14])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 680234-FluorobenzaldehydeHCID 517165Ammonium Acetate

Produkt 1

HCID 5798853-Amino-3-(4-fluorophenyl)propanoic acidAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Fluorobenzaldehyde (10 g, 80 mmol), ammonium acetate (8.2487 g, 107 mmol) and malonic acid (8.3285 g, 80 mmol) were refluxed (slow) in absolute ethanol (60 mL) for 48 hours. White solid was filtered and purified by ethanol recrystallization to afford β-4-fluorophenyl-β-alanine (10.04 g, 54.8 mmol, 68.5%); MP: 216-217° C.; IR (KBr): 3160, 1606 cm−1; TLC: RF=0.41 (solvent 24), 0.42 (solvent 25); 1H NMR (D2O/K2CO3): δ 7.28-7.19 (m, 2H), 7.03-6.91 (m, 2H), 4.10 (t, J=7.39 Hz, 1H), 2.54-2.34 (m, 2H). Anal. Calcd for C9H10FNO2.5/3H2O: C, 50.70; H, 6.30; N, 6.57. Found: C, 50.34; H, 6.39; N, 6.30.

Aufarbeitung

  1. filtrationWhite solid was filtered
  2. custompurified by ethanol recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-aeb9d77789e44df3ab74d9a2e0f0dd6b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268164B2

Notizen zur Reaktion

Wird geladen…