Glycine → HCID 135879570, compound

HRID 2388151Notes

Reaction equation

HRID 2388151 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:13][C:9]2=[C:10]([CH3:12])[N:11]=1)=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26].C[O-].[Na+]>CO>[OH:22][C:7]1[C:6]([C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5])=[N:11][C:10]([CH3:12])=[C:9]2[O:13][N:14]=[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:8]=12

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 136399880HCID 136399880, compound

Product 1

HCID 135879570HCID 135879570, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-7-methyl-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (93 mg, 0.31 mmol), glycine (470 mg, 6.27 mmol), and a 0.5 M solution sodium methoxide in methanol (11.9 ml) was refluxed for 42 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 ml) and the solution was extracted with methyl t-butyl ether (2×25 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 gray solid (89 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.25 (t, 1H), 8.03 (m, 2H), 7.57 (m, 3H), 4.01 (d, J=6.2 Hz, 2H), 2.71 (s, 3H); MS: (+) m/z 327.98 (M+1), (−) m/z 325.99 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (20 ml)
  3. extractionthe solution was extracted with methyl t-butyl ether (2×25 ml)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6e5397fbb88d436bac3e77d78b9b2bee
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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