Lithium Hydroxide → 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid

HRID 1095927Notes

Reaction equation

HRID 1095927 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:33])[C:20]([OH:32])([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=3)[C:21]([F:24])([F:23])[F:22])=[C:15]([Cl:34])[CH:14]=2)=[CH:7][CH:6]=1)C.[Li+].[OH-]>C1COCC1.CO>[Cl:34][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[CH:19]([CH3:33])[C:20]([OH:32])([C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=1)[C:21]([F:23])([F:24])[F:22])[O:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:35])=[O:3])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 469406434-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid ethyl ester

Product 1

HCID 469406444-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxymethyl}-benzoic acid ethyl ester (250 mg) was dissolved in THF/methanol=5/1 (6 mL) followed by the addition of aqueous LiOH solution (1.0M, 0.54 mL). The mixture was heated to 50° C. for 3.5 hours. The reaction was cooled and concentrated in vacuo. The residue was dissolved in water (5 mL) and aqueous HCl solution (1.0M, 0.54 mL) was added. The mixture was stirred at r.t. for 15 minutes and then at 0° C. for 1 hour. The resulting precipitate was filtered off and washed with cold water. The residual water was removed by co-evaporation with toluene. The resulting solid was dried in vacuo. The title compound was obtained as a colorless solid (220 mg, 93%). MS (m/e)=480.1 [MH+].

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (5 mL)
  4. additionaqueous HCl solution (1.0M, 0.54 mL) was added
  5. waitat 0° C. for 1 hour
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with cold water
  8. customThe residual water was removed by co-evaporation with toluene
  9. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-3f4698f6137f446a9b1952a18c949c04
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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