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

HRID 2388169
Notes
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Reaction equation

HRID 2388169 reaction equation
[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].[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][CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67530168HCID 67530168, compound

Product 1

HCID 42635754[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 57.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

Ethyl 7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (0.11 g, 0.39 mmol) was dissolved in 10 mL of DMF. Glycine (0.58 g, 7.75 mmol) and sodium ethoxide (0.40 g, 5.81 mmol) were added and the mixture was refluxed for 14 h. The mixture was cooled to room temperature and diluted with 60 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 70 mg of the title compound. MS: (+) m/z 314.00 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 14 h
  2. filtrationThe resulting suspension was filtered
  3. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-cb13ec805d4e42768ba1745a7a37292d
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08269008B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes