Beta-Alanine → 3-[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

HRID 1480931Notes

Reaction equation

HRID 1480931 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].CO>C[O-].[Na+]>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:4]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 887MethanolHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 717351373-[(4-Hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (185 mg, 0.55 mmol), beta-alanine (489 mg, 5.5 mmol) in 0.5 M NaOMe in MeOH solution (8.8 mL, 4.4 mmol) was refluxed overnight. After cooled, the reaction mixture was concentrated and residue was dissolved in water (80 mL). It was acidified by 1 N HCl solution to pH ca. 3-4. Resulting gummy solid was collected by filtration, rinsed with water and then dissolved in EtOAc. The organic solution was dried over MgSO4, filtered and concentrated to provide the title compound (173 mg, 0.49 mmol) as an off-white solid in 89% yield. LC-MS ESI−: 351.14 (M−1)−.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooled
  3. concentrationthe reaction mixture was concentrated
  4. dissolutionresidue was dissolved in water (80 mL)
  5. filtrationResulting gummy solid was collected by filtration
  6. washrinsed with water
  7. dissolutiondissolved in EtOAc
  8. dry with materialThe organic solution was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-216f22b7fe6742a38aae8e73d2589926
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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