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

HRID 2187365Notes

Reaction equation

HRID 2187365 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 chromatog,raphed (silica gel, 80% ethyl acetate/hexane, then ethyl acetate) to give ester 1-4 as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customremoval of the solvent

Sources & evidence

ORD record
ord-952334d0ecf54cec9fa075b71e4da90d
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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