Glycine → [(7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 2388135Notes

Reaction equation

HRID 2388135 reaction equation
CO[C:3]([C:5]1[N:10]=[CH:9][C:8]2[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:7]=2[C:6]=1[OH:20])=[O:4].[NH2:21][CH2:22][C:23]([OH:25])=[O:24]>C[O-].[Na+].CO>[OH:20][C:6]1[C:7]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:11][C:8]=2[CH:9]=[N:10][C:5]=1[C:3]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:4]

Participants

5

Reactant 2

HCID 750GlycineHCID 675295697-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 42634663[(7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (100 mg, 0.37 mmol), and glycine (583 mg, 7.77 mmol) were suspended in 14.8 mL of 0.5N sodium methoxide in methanol. The reaction mixture was heated at reflux temperature overnight, then cooled, and concentrated. The residue was dissolved in water (30 mL), and the solution was acidified to pH 1-2 with 2N HCl, and subsequently extracted with ethyl acetate. The combined organic layers were dried, and concentrated to produce 104 mg of the title compound as a yellow solid. MS: (+) m/z 314.0 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water (30 mL)
  6. extractionsubsequently extracted with ethyl acetate
  7. customThe combined organic layers were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50b331699f4841ac83b0007a31e40183
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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