Glycine → {[7-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388145Notes

Reaction equation

HRID 2388145 reaction equation
CO.C[O-].[Na+].C[O:7][C:8]([C:10]1[N:15]=C(C2C=CC=C(OC)C=2)C2N=C(C3C=CC=CC=3)OC=2C=1OC(=O)C(C)(C)C)=[O:9].CO[C:42]([C:44]1[N:49]=[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=2)[C:47]2[N:58]=[C:59]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[O:60][C:46]=2[C:45]=1[OH:67])=[O:43].NCC(O)=O>CO>[OH:67][C:45]1[C:46]2[O:60][C:59]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[N:58][C:47]=2[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=2)=[N:49][C:44]=1[C:42]([NH:15][CH2:10][C:8]([OH:9])=[O:7])=[O:43]

Participants

6

Reactant 4

HCID 750GlycineHCID 23694274Sodium methanolate methanol2×HCID 675295117-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl esterHCID 675305517-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 42634847{[7-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 350.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide methanol solution (0.5 N, 0.4 mL, 0.2 mmol) was added to a solution of 7-(2,2-dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (7.5 mg, 0.016 mmol), and 7-hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (24.7 mg, 0.066 mmol) in methanol (2 mL) at room temperature. After the reaction mixture was refluxed for 1 hour, the mixture was concentrated. To the residue glycine (0.129 g, 1.72 mmol) and sodium methoxide methanol solution (0.5 N, 2.88 mL, 1.44 mmol) were then added. The mixture was then refluxed overnight, cooled, and concentrated. The residue was dissolved in water (30 mL), and the solution was washed with ethyl acetate (3×20 mL). After the solution was acidified to pH 1-2 with 2N HCl, a light yellow solid precipitated, that was collected by filtration and then dried in vacuo to give 23.5 mg of the title compound. MS: (−) m/z 417.9 (M−1).

Workup

  1. temperatureAfter the reaction mixture was refluxed for 1 hour
  2. concentrationthe mixture was concentrated
  3. temperatureThe mixture was then refluxed overnight
  4. temperaturecooled
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in water (30 mL)
  7. washthe solution was washed with ethyl acetate (3×20 mL)
  8. customa light yellow solid precipitated
  9. filtrationthat was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-8a76c20c05cf4478b330ab325577febe
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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