Glycine → {[7-Hydroxy-3-(4-methoxy-phenyl)-4-methyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388221Notes

Reaction equation

HRID 2388221 reaction equation
[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:9]

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67530662HCID 67530662, compound

Product 1

HCID 42633244{[7-Hydroxy-3-(4-methoxy-phenyl)-4-methyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 48.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-methylisoxazolo[4,5-c]pyridine-6-carboxylate (35 mg, 0.11 mmol) and glycine (320 mg, 4.27 mmol) were added to sodium methoxide solution (6.4 mL, 3.20 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in minimum amount of water and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 22 mg of crude solid. The solid was dissolved in 10 mL of saturated sodium bicarbonate solution and washed with hexanes and EtOAc. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 19 mg of the title compound. MS: (+) m/z 358.37 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in minimum amount of water and 0.25 M hydrochloric acid
  4. additionwas added until pH was 3
  5. customThe precipitate was isolated by filtration
  6. customdried under vacuum
  7. customto give 22 mg of crude solid
  8. washwashed with hexanes and EtOAc
  9. extractionextracted with EtOAc
  10. dry with materialThe organic layer was dried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-dcbf544c47ab4938893bf063bb3d80f4
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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