L-Proline → Methyl 5-(1,8-naphthyridin-2-yl)pentanoate

HRID 1004234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1004234
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=O)[CH3:9].[NH2:12][C:13]1[C:18]([CH:19]=O)=[CH:17][CH:16]=[CH:15][N:14]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 145742L-ProlineHCID 288022Heptanoic acid, 6-oxo-, methyl esterHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Produkt 1

HCID 11447926Methyl 5-(1,8-naphthyridin-2-yl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-2 (1.4 g, 9.04 mmol), 1-3, 2-amino-3-formylpyridine (552 mg, 4.52 mmol) (for preparation, see: J. Org. Chem., 1983, 48, 3401), and proline (260 mg, 2.26 mmol) in absolute ethanol (23 mL) was heated at reflux for 18 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 80% ethyl acetate/hexane, then ethyl acetate) to give ester 1-4 as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 80% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ea773409006d4e579198480a224f565c
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048861

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