Glycine → HCID 135879571, compound

HRID 2388153Notes

Reaction equation

HRID 2388153 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:27])=[C:8]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][O:18][C:9]2=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+]>CO>[OH:27][C:7]1[C:6]([C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5])=[N:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:9]2[O:18][N:19]=[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:8]=12

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 136399881HCID 136399881, compound

Product 1

HCID 135879571HCID 135879571, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-3,7-diphenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (86 mg, 0.24 mmol), glycine (360 mg, 4.79 mmol), and a 0.5 M solution of sodium methoxide in methanol (9.1 ml) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 ml) and the resulting solution extracted with methyl t-butyl ether (3×25 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 white solid (80 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 390.27 (M+1).

Workup

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

Sources & evidence

ORD record
ord-58ecd9ff12f942ea80388afd2552c870
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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