Lithium Hydroxide → HCID 11611416, compound

HRID 751181Notes

Reaction equation

HRID 751181 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)C.[Li+].[OH-]>C1COCC1.CO>[F:30][C:28]([F:29])([F:31])[O:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][CH2:18][CH2:17][CH2:16][O:15][C:12]2[CH:13]=[C:14]3[C:9]([CH:8]=[CH:7][N:6]3[CH2:5][C:4]([OH:32])=[O:3])=[CH:10][CH:11]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68826126{6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester

Product 1

HCID 11611416HCID 11611416, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of {6-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester (30 mg, 67 μmol) in THF/methanol 2/1 (1.5 ml) was added 1 N aqueous LiOH solution (400 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 (28 mg, 67 μmol, quant.) 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-1304fb2de09b456bbbee78a5dc4fd505
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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