Glycine → {[7-Hydroxy-3-(4-methoxy-phenyl)-4-pyrazol-1-ylmethyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388231Notes

Reaction equation

HRID 2388231 reaction equation
[N:1]1([CH2:6][C:7]2[C:12]3[C:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)=[N:14][O:15][C:11]=3[C:10]([OH:24])=[C:9]([C:25](OCC)=[O:26])[N:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>>[OH:24][C:10]1[C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:12]=2[C:7]([CH2:6][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:8][C:9]=1[C:25]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:26]

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67529978Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633436{[7-Hydroxy-3-(4-methoxy-phenyl)-4-pyrazol-1-ylmethyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 68.9%

Procedure

Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (19 mg, 0.048 mmol) and glycine (181 mg, 2.41 mmol) were added to sodium methoxide solution (3.6 mL, 1.81 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 10 mL of water, and washed with EtOAc. The aqueous layer was acidified to pH 3 with 4M hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 14 mg of the title compound. MS: (+) m/z 424.31 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 10 mL of water
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d1dcc7b6de24588a9c63242cafdc0f8
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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