Lithium Hydroxide → HCID 66749337, compound

HRID 537071Notes

Reaction equation

HRID 537071 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:17]([O:19]CC)=[O:18])=[C:14]([I:16])[N:15]=2)[C:8]([CH3:22])=[CH:7][N:6]=1)(=[O:3])[CH3:2].[Li+].[OH-]>C1COCC1.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:17]([OH:19])=[O:18])=[C:14]([I:16])[N:15]=2)[C:8]([CH3:22])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66749451HCID 66749451, compound

Product 1

HCID 66749337HCID 66749337, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2-acetamido-5-methylpyridin-4-yl)-4-iodo-1,3-oxazole-5-carboxylate (33.0 g, 80.0 mmol) in THF (660 mL) was added an aqueous solution of LiOH (1M in water, 80 mL). The reaction mixture was allowed to stir for 5 h and then diluted with water. The organic solvent was removed by evaporation and the pH of the remaining aqueous solution was adjusted to 3-4. The mixture was filtered and the solid was collected, washed with water, and dried to give 2-(2-acetamido-5-methylpyridin-4-yl)-4-iodo-1,3-oxazole-5-carboxylic acid (25.0 g, 81%).

Workup

  1. customThe organic solvent was removed by evaporation
  2. filtrationThe mixture was filtered
  3. customthe solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-338a43f82de74bb79cd6f30a63b994ce
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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