Lithium hydroxide, monohydrate → 4-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid

HRID 494317Notes

Reaction equation

HRID 494317 reaction equation
C[O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:10]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH:9]=1)=[O:4].O[Li].O>C1COCC1.CO.O>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]=1[C:10]([C:8]1[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][CH:7]=1)=[O:11]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 576831324-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 574577094-(5-Methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.2 g (4 mmol) 4-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-1H-pyrrole-2-carboxylic acid methyl ester and 1.3 g (31 mmol) LiOH.H2O in 40 mL THF, 5 mL methanol and 10 mL water was heated to reflux for 3 h. The mixture was concentrated, acidified and extracted with ethyl acetate. The combined organic extracts were dried with Na2SO4 and evaporated to yield 1.1 g (96%) of the title compound as light yellow solid. (m/e): 295.1 (M−; 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-1e3e514fd1da4578816c30af640e5fd3
Source dataset
uspto-grants-2009_05
Patent number
US07538132B2

Reaction notes

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