Hydrochloric Acid → HCID 68157828, compound

HRID 537505Notes

Reaction equation

HRID 537505 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][CH:4]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:24]=[CH:23]2)=[CH:18][CH:17]=1)[O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][CH:2]([CH3:31])[CH2:3][CH:4]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[C:25]([C:27]([F:29])([F:28])[F:30])[N:24]=[CH:23]2)=[CH:18][CH:17]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68156679HCID 68156679, compound

Product 1

HCID 68157828HCID 68157828, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzoate (65 mg, 0.15 mmol) was dissolved in methanol (1.5 mL) and 1M NaOH (0.75 mL) was added at room temperature. The resulting mixture was stirred overnight. The reaction mixture was diluted with water (10 mL), acidified with 1M HCl (1 mL) and extracted with ethyl acetate (2×10 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give (+/−)-4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzoic acid (65 mg, 100%) as a gum. 1H NMR (400 MHz, CDCl3, δ): 7.98 (d, J=9 Hz, 2H), 7.88 (s, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.58 (s, 1H), 7.39 (d, J=8.5 Hz, 2H), 6.89 (d, J=8.8 Hz, 2H), 5.33 (dd, J=9, 4.6 Hz, 1H), 2.05 (m, 1H), 1.96-1.83 (m, 1H), 1.67-1.60 (m, 1H), 1.04 (d, J=6.6 Hz, 3H), 0.99 (d, J=6.6 Hz, 3H). MS (M+1): 419.0.

Workup

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16a8cc4537b748fda7710a224e891b34
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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