Beta-Alanine → 3-[(4-Hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]propionic acid

HRID 1410793Notes

Reaction equation

HRID 1410793 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:16])[NH:10][CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C[O-].[Na+]>>[OH:15][C:14]1[C:13]2[CH:12]=[CH:11][NH:10][C:9](=[O:16])[C:8]=2[CH:7]=[N:6][C:5]=1[C:3]([NH:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:4]

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 10942334Sodium MethoxideHCID 682972414-Hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 682974673-[(4-Hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]propionic acidYield 89%

Procedure

A mixture of 4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (17 mg, 0.077 mmol), β-alanine (138 mg, 1.55 mmol) and NaOMe solution (2.3 mL, 1.16 mmol, 0.5 M in MeOH) was refluxed for 16 h. Solvent was evaporated in vacuo, and the residue was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified with 4 M HCl to pH about 1, and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 19 mg of the title compound as an off-white solid. MS: (+) m/z 278.21 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. customSolvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in saturated NaHCO3
  4. washwashed several times with ether
  5. extractionthe resulting mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da0880f6154f4112aa6e665ace2d904a
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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