Tetrahydrofuran → 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoic acid

HRID 541385Notes

Reaction equation

HRID 541385 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([C:5]1[NH:9][C:8]([C:10]2[C:11]([CH3:21])=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=2)[C:15]([O:17]C)=[O:16])=[N:7][CH:6]=1)=[O:4].O1CCCC1>[Li+].[OH-]>[CH3:1][N:2]([CH3:22])[C:3]([C:5]1[NH:9][C:8]([C:10]2[C:11]([CH3:21])=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=2)[C:15]([OH:17])=[O:16])=[N:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 68288243Methyl 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoate2×

Product 1

HCID 682891005-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoic acidYield 53%

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent

Procedure

Methyl 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoate (compound 232.1, 113 mg, 0.37 mmol) was dissolved in 2N LiOH aqueous (1 ml) and tetrahydrofuran (THF) (5 ml) and heated to 50° C. for 16 hours. After cooling to ambient temperature, the organic solvent was removed in vacuo. The pH of the remaining aqueous layer was adjusted with 2N HCl to pH 3-4. The resulting precipitate was collected by filtration and dried to afford 56 mg of 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoic acid (53%). m/z (ES+) 288 (M+H)+.

Workup

  1. customthe organic solvent was removed in vacuo
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-efca134619974763875ddb5ff1561c59
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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