L-Alanine → HCID 54746589, compound

HRID 2190936Notes

Reaction equation

HRID 2190936 reaction equation
CO[C:3]([C:5]1[C:6](=[O:25])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH:11]=[CH:10][CH:9]=2)=[O:4].[NH2:26][C@H:27]([C:29]([OH:31])=[O:30])[CH3:28].C[O-].[Na+]>COCCO>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:16][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[C:14]([OH:15])=[C:5]([C:3]([NH:26][C@@H:27]([CH3:28])[C:29]([OH:31])=[O:30])=[O:4])[C:6](=[O:25])[O:7]3)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 86649472HCID 86649472, compound

Product 1

HCID 54746589HCID 54746589, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 5-(4-fluoro-benzyloxy)-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (86 mg, 0.25 mmol) and L-alanine (334 mg, 3.75 mmol) in 2-methoxyethanol was added sodium methoxide (176 mg, 3.25 mmol). Resulting mixture was refluxed overnight and concentrated. Residue was dissolved in water (100 mL) and acidified using 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried. Crude product was triturated with MeOH. Solid was collected and dried in vacuo to provide the title compound (61 mg). MS ESI(+) m/e: 402.13 (M+1).

Workup

  1. customResulting mixture
  2. temperaturewas refluxed overnight
  3. concentrationconcentrated
  4. dissolutionResidue was dissolved in water (100 mL)
  5. customPrecipitate was collected
  6. washrinsed with water
  7. customdried
  8. customCrude product was triturated with MeOH
  9. customSolid was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0b62d5a81cec45de92ace505752be95d
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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