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

HRID 2388209Notes

Reaction equation

HRID 2388209 reaction equation
[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:23][CH2:24][C:25]([OH:27])=[O:26].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67530597Ethyl 7-hydroxy-4-methyl-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633064[(7-Hydroxy-4-methyl-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 7-hydroxy-4-methyl-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (41 mg, 0.138 mmol) was dissolved in 5 mL of DMF. Glycine (207 mg, 2.75 mmol) and sodium ethoxide (140 mg, 2.06 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 30 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 3. The aqueous phase was extracted with EtOAc and the combined organic layer was dried over MgSO4 and concentrated to give 35 mg of pale yellow solid. The solid was dissolved in saturated NaHCO3 (10 mL) and washed with hexanes and EtOAc. The aqueous phase was acidified to pH 3 with concentrated HCl and extracted with EtOAc. The organic layer was dried and concentrated to give 15 mg of the title compound. MS: (+) m/z 328.39 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7ce78763ac614eae9f0c9c04ffaa3e47
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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