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

HRID 2388219Notes

Reaction equation

HRID 2388219 reaction equation
[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:4]=2[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:4]=2[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:6][C:7]=1[C:8]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:9]

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67531952Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633243{[7-Hydroxy-3-(4-methoxy-phenyl)-4-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 62.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (70 mg, 0.18 mmol) and glycine (539 mg, 7.18 mmol) were added to sodium methoxide solution (10.8 mL, 5.38 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 79 mg of crude solid. The solid was dissolved in 15 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 the precipitate was collected by filtration. The solid was dried under vacuum to afford 47 mg of the title compound. MS: (+) m/z 420.37 (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 79 mg of crude solid
  8. washwashed with hexanes and EtOAc
  9. filtrationthe precipitate was collected by filtration
  10. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-06a55c5459114adf9747edcf121160c7
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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