Hydrochloric Acid → HCID 23510774, compound

HRID 1883475Notes

Reaction equation

HRID 1883475 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[O:9])[N:4]=[C:3]1[C:24]([O:26]CC)=[O:25].[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:9])[N:4]=[C:3]1[C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23510773HCID 23510773, compound

Product 1

HCID 23510774HCID 23510774, compoundYield 80.94%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylate (0.69 g, 1.65 mmol) prepared in the capping step was dissolved in THF/H2O (27.40 ml/13.70 ml), 1N LiOH (4.57 ml) was added thereto, and the mixture was stirred at room temperature. After 15 hours have passed, the reaction solution was acidified to pH 2.0 by 1N HCl and then extracted with EA and water. The organic layer was washed with aqueous NaCl solution, dried over anhydrous MgSO4, and concentrated. The residue was recrystallized from EA and n-hexane to give 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid (0.52 g, 80.94%) of a white solid.

Workup

  1. extractionextracted with EA and water
  2. washThe organic layer was washed with aqueous NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was recrystallized from EA and n-hexane

Sources & evidence

ORD record
ord-207a690ac1ec41ccb6734b12dbb40251
Source dataset
uspto-grants-2004_07
Patent number
US06759511B2

Reaction notes

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