Hydrochloric Acid → HCID 68706799, compound

HRID 2240164Notes

Reaction equation

HRID 2240164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH2:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:25][C@@H:26]1[CH2:30][CH2:29][O:28][CH2:27]1.O1CCOCC1.[OH-].[Na+].Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:25][C@@H:26]1[CH2:30][CH2:29][O:28][CH2:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 68713773HCID 68713773, compound

Product 1

HCID 68706799HCID 68706799, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Into a 1-neck round-bottom flask was added methyl 4-[(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)methyl]benzoate (330 mg, 0.808 mmol), 5 mL of 1,4-dioxane, 20 mL of water and 8 mL of 2 M aqueous sodium hydroxide. The reaction was heated at 90° C. for 1.5 hours, acidified with 1N HCl until pH˜3 and extracted with 3×20 mL CH2Cl2. The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 4-[(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)methyl]benzoic acid (260 mg, 81%) as a brown solid. LCMS M+1=395.2

Workup

  1. extractionextracted with 3×20 mL CH2Cl2
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-937972117a584eabb539fb8e1c440ca8
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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