Water → HCID 68156708, compound

HRID 537521Notes

Reaction equation

HRID 537521 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:33])[C:23]=1[N:24]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[N:25]1)[O:5][CH:6]([C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=1)[CH2:7][CH2:8][CH3:9].O.O1CCCC1.O.[OH-].[Li+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:33])[C:23]=1[N:24]1[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[N:25]1)[O:5][CH:6]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:19][CH:20]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68156951HCID 68156951, compound

Product 1

HCID 68156708HCID 68156708, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vial containing ethyl 4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoate (135 mg, 0.29 mmol) was added water (0.59 mL), tetrahydrofuran (0.591 mL), and methanol (0.59 mL). Lithium hydroxide monohydrate (615.0 mg, 14.6 mmol) was then added. The suspension was stirred at room temperature for 18 hours. The reaction was concentrated in vacuo. The residue was acidified to pH=3 with citric acid (5%). The mixture was extracted three times with ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated to give (+/−)-4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoic acid (120 mg, 95%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.07 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 7.65 (s, 1H), 7.45 (d, J=8.2 Hz, 2H), 6.58 (s, 2H), 5.18 (dd, J=8.0, 4.9 Hz, 1H), 2.04-1.92 (m, 1H), 1.89 (s, 6H), 1.87-1.75 (m, 1H), 1.61-1.36 (m, 2H), 0.97 (t, J=7.4 Hz, 3H). MS (M+1): 433.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7aee667c7f648a89c29a1caf4e0c2b7
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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