Glycine → HCID 135879557, compound

HRID 2388148Notes

Reaction equation

HRID 2388148 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][O:12][C:9]2=[CH:10][N:11]=1)=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].C[O-].[Na+]>CO>[OH:21][C:7]1[C:6]([C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5])=[N:11][CH:10]=[C:9]2[O:12][N:13]=[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]=12

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 136399878HCID 136399878, compound

Product 1

HCID 135879557HCID 135879557, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (61 mg, 0.21 mmol), glycine (322 mg, 4.29 mmol), and a 0.5 M solution of sodium methoxide in methanol (8.1 ml) was refluxed for 20 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (15 ml) and the solution was extracted with methyl t-butyl ether (2×20 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl. The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (26 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.47 (br s, 1H), 8.82 (s, 1H), 8.04 (m, 2H), 7.59 (m, 3H), 4.01 (d, J=6.4 Hz, 2H); MS: (+) m/z 314.07 (M+1), (−) m/z 312.20 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (15 ml)
  3. extractionthe solution was extracted with methyl t-butyl ether (2×20 ml)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-634602e8f2da40558a7fc8d6f673096a
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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