Lithium Hydroxide → HCID 178525824, compound

HRID 915385

Reaction equation

HRID 915385 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)[NH:21][N:20]=3)[CH:15]=2)[CH:10]=[CH:9]1)(C)(C)C.[Li+].[OH-]>C1COCC1.CO>[F:33][C:30]([F:31])([F:32])[C:27]1[CH:28]=[CH:29][C:24]([C:22]2[NH:21][N:20]=[C:19]([CH2:18][O:17][C:14]3[CH:15]=[C:16]4[C:11]([CH:10]=[CH:9][N:8]4[CH2:7][C:6]([OH:34])=[O:5])=[CH:12][CH:13]=3)[CH:23]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178451203[6-[5-(4-Trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 178525824HCID 178525824, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of {6-[5-(4-trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester (5 mg, 10 μmol) in THF/methanol 2/1 (750 μl) was added 1 N aqueous LiOH solution (600 μl). The reaction mixture was stirred for 14 h at ambient temperature and concentrated under reduced pressure. The residue was dissolved in 1 N HCl/ice water 1/1 and ethyl acetate, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give the title compound (3 mg, 7 μmol, 68%) as brown crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 N HCl/ice water 1/1
  3. customethyl acetate, the layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a94aae4837e540aa941581e8a68394ae
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Linked notes

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