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

HRID 2388185Notes

Reaction equation

HRID 2388185 reaction equation
[OH:1][C:2]1[C:3]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:4]=2[CH:5]=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:24][CH2:25][C:26]([OH:28])=[O:27].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67530073Ethyl 7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633060{[7-Hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (0.12 g, 0.38 mmol) was dissolved in 10 mL of DMF. Glycine (0.574 g, 7.64 mmol) and sodium ethoxide (0.391 g, 5.73 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 70 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 3. The resulting suspension was filtered and the solid was dried under vacuum to give 94 mg of the title compound. MS: (+) m/z 344.37 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. filtrationThe resulting suspension was filtered
  3. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-a6765a6727c347c8953045afb8f5eb7a
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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