Glycine → HCID 42633246, compound

HRID 2388225Notes

Reaction equation

HRID 2388225 reaction equation
[OH:1][C:2]1[C:3]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[C:5]([C:13]#[C:14][Si](C)(C)C)=[N:6][C:7]=1[C:8](OCC)=[O:9].C[O-].[Na+].[NH2:31][CH2:32][C:33]([OH:35])=[O:34]>C(=O)(O)[O-].[Na+]>[C:13]([C:5]1[C:4]2[C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][C:3]=2[C:2]([OH:1])=[C:7]([C:8]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:9])[N:6]=1)#[CH:14]

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67532332HCID 67532332, compound

Product 1

HCID 42633246HCID 42633246, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 7-hydroxy-3-phenyl-4-((trimethylsilyl)ethynyl)isoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.53 mmol) was added to sodium methoxide solution (39.5 mL, 19.7 mmol, 0.5 M in MeOH) and the mixture was refluxed for 30 min. After the mixture was cooled to room temperature, glycine (1.98 g, 26.3 mmol) was added, 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 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 170 mg of crude solid. The solid was dissolved in 100 mL of saturated sodium bicarbonate solution and washed with EtOAc. The aqueous layer was acidified with concentrated hydrochloric acid to pH 3 and extracted with EtOAc. The solvent was concentrated in vacuo to give 116 mg of the title compound. MS: (−) m/z 336.28 (M−1).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. temperaturethe mixture was refluxed for 48 h
  3. temperatureThe mixture was cooled to room temperature
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in 100 mL of water
  6. additionhydrochloric acid was added until pH was 3
  7. customThe precipitate was isolated by filtration
  8. customdried under vacuum
  9. customto give 170 mg of crude solid
  10. washwashed with EtOAc
  11. extractionextracted with EtOAc
  12. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-e9239f5f0dc54b8b814a289bccb45e26
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…