Glycine → HCID 42633245, compound

HRID 2388223Notes

Reaction equation

HRID 2388223 reaction equation
[OH:1][C:2]1[C:3]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:4]=2[C:5]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>>[OH:1][C:2]1[C:3]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:4]=2[C:5]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6][C:7]=1[C:8]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:9]

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67529979HCID 67529979, compound

Product 1

HCID 42633245HCID 42633245, compoundYield 82.1%

Procedure

Ethyl 7-hydroxy-3-phenyl-4-(phenylethynyl)isoxazolo[4,5-c]pyridine-6-carboxylate (195 mg, 0.51 mmol) and glycine (1.9 g, 25.3 mmol) were added to sodium methoxide solution (38 mL, 19.0 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in 100 mL of water and hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 173 mg of the title compound. MS: (+) m/z 414.32 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 100 mL of water
  4. additionhydrochloric acid was added until pH was 3
  5. customThe precipitate was isolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-91272479d8f44da4aa016c7890512920
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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