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

HRID 2388198
Notes
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Reaction equation

HRID 2388198 reaction equation
[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][N: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.CCOC(C)=O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][N: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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67529597HCID 67529597, compound

Product 1

HCID 42633062[(7-Hydroxy-3-pyridin-4-yl-isoxazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 28.9%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-hydroxy-3-(pyridin-4-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (95 mg, 0.33 mmol) was dissolved in 10 mL of DMF. Glycine (500 mg, 6.67 mmol) and sodium ethoxide (340 mg, 5.0 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 50 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 3. EtOAc (50 mL) was added to the resulting suspension, and the mixture was transferred to a separatory funnel. The aqueous layer was removed, and the organic layer, which contained an insoluble solid, was filtered. The solid was dried under vacuum to give 30 mg of the title compound. MS: (+) m/z 315.34 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customthe mixture was transferred to a separatory funnel
  3. customThe aqueous layer was removed
  4. filtrationwas filtered
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-1b8d80cda14d42569d980ba5874576df
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