Methanol → HCID 68156518, compound

HRID 537554Notes

Reaction equation

HRID 537554 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([CH3:36])[C:26]=1[N:27]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[N:28]1)[O:5][CH:6]([CH:18]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19]1)[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][CH:8]=1.O1CCCC1.CO.[OH-].[Na+]>O>[CH3:36][C:25]1[CH:24]=[C:4]([CH:3]=[C:2]([CH3:1])[C:26]=1[N:27]1[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[N:28]1)[O:5][CH:6]([CH:18]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19]1)[C:7]1[CH:17]=[CH:16][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68157679HCID 68157679, compound

Product 1

HCID 68156518HCID 68156518, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing ethyl 4-((3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)(3,3-dimethylcyclobutyl)methyl)benzoate (135 mg, 0.270 mmol) was added anhydrous tetrahydrofuran (0.680 mL), methanol (0.680 mL), water (0.680 mL) and sodium hydroxide (55.7 mg, 1.35 mmol). After 8 h, the reaction was concentrated and dissolved in ethyl acetate and water. 1 N hydrochloric acid was added to pH 3 and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give 4-((3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)(3,3-dimethylcyclobutyl)methyl)benzoic acid (110 mg, 86% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 8.06 (d, J=8.2 Hz, 2H), 7.88 (s, 1H), 7.65 (s, 1H), 7.41 (d, J=8.4 Hz, 2H), 6.58 (s, 2H), 5.03 (d, J=6.8 Hz, 1H), 2.80-2.55 (m, 1H), 2.07-1.72 (m, 9H), 1.67 (dd, J=8.2, 3.5 Hz, 1H), 1.14 (s, 3H), 1.10 (s, 3H). MS (M+1): 473.5.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. addition1 N hydrochloric acid was added to pH 3
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22e5e552cd2744958e6dfe81e23e745e
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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