Hydrochloric Acid → HCID 11166570, compound

HRID 890437Notes

Reaction equation

HRID 890437 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]3[C:20]([CH3:35])=[N:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)[CH:15]=2)[CH:10]=[CH:9]1)(C)(C)C.[Li+].[OH-].Cl>C1COCC1.CO>[CH3:35][C:20]1[C:19]([CH2:18][O:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][N:8]3[CH2:7][C:6]([OH:36])=[O:5])=[CH:12][CH:13]=2)=[CH:24][CH:23]=[C:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=2)[N:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69642195{6-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11166570HCID 11166570, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of {6-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester (20 mg, 0.04 4 μmol) in THF/methanol 2/1 (3 ml) was added a 1 N aqueous LiOH solution (1 ml). The reaction mixture was stirred for 14 h at ambient temperature, neutralized with 1 N aqueous HCl solution under ice cooling 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 (18 mg, 0.04 μmol, quant.) as white solid.

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-4771919e49ec42cfb690c7ae7de045eb
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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