Lithium Hydroxide → HCID 67133045, compound

HRID 545360Notes

Reaction equation

HRID 545360 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH:27]2[CH2:29][CH2:28]2)[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[N:9][C:10]=1[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O.CCOC(C)=O>[CH:27]1([N:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:18][CH:17]=2)[CH2:29][CH2:28]1

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 67133207HCID 67133207, compound

Product 1

HCID 67133045HCID 67133045, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.076 g (1.87 mmol) of 3-cyclopropyl-5-furan-2-yl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester and 0.013 g (5.42 mmol) of LiOH in 4 ml of THF, 2 ml of MeOH and 2 ml of H2O was stirred at 80° C. for 4.5 hours. The reaction mixture was then cooled to RT, diluted with EtOAc and washed with 10% KHSO4 solution and brine. The aqueous phases were extracted twice with EtOAc. The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give 69 mg (96%) of the title compound as white powder. MS: 377.1 (MH+).

Workup

  1. washwashed with 10% KHSO4 solution and brine
  2. extractionThe aqueous phases were extracted twice with EtOAc
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f57f301cdc854d4c8cb64dd6dac2c06f
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

Loading…