Glycine → HCID 42633242, compound

HRID 2388217Notes

Reaction equation

HRID 2388217 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[C:11]3[C:12]([C:22]#[N:23])=[N:13][C:14]([C:17](OCC)=[O:18])=[C:15]([OH:16])[C:10]=3[O:9][N:8]=2)=[CH:4][CH:3]=1.[NH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[O:6][C:5]([C:7]2[C:11]3[C:12]([C:22]#[N:23])=[N:13][C:14]([C:17]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:18])=[C:15]([OH:16])[C:10]=3[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67530700Ethyl 3-(5-bromofuran-2-yl)-4-cyano-7-hydroxyisoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633242HCID 42633242, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 3-(5-bromofuran-2-yl)-4-cyano-7-hydroxyisoxazolo[4,5-c]pyridine-6-carboxylate (42 mg, 0.11 mmol) and glycine (334 mg, 4.44 mmol) were added to sodium methoxide solution (6.7 mL, 3.33 mmol, 0.5 M in MeOH) and the mixture was refluxed for 48 h. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was redissolved in a minimum amount of water, and 0.25 M hydrochloric acid was added until pH was 3. The resulting precipitate was isolated by filtration and dried under vacuum to give 21 mg of crude solid. The solid was dissolved in 10 mL of saturated sodium bicarbonate solution and washed with hexanes and EtOAc. The aqueous layer was acidified to pH 3 and extracted with EtOAc. The combined organic layer was dried over MgSO4 and concentrated to afford 10 mg of the title compound. MS: (−) m/z 405.21, 407.18 (M−1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 48 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was redissolved in a minimum amount of water, and 0.25 M hydrochloric acid
  4. additionwas added until pH was 3
  5. customThe resulting precipitate was isolated by filtration
  6. customdried under vacuum
  7. customto give 21 mg of crude solid
  8. washwashed with hexanes and EtOAc
  9. extractionextracted with EtOAc
  10. dry with materialThe combined organic layer was dried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f6945f289c9c419abb8f9896edc7e716
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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