Sodium Hydroxide → 4-Cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoic acid

HRID 541398Notes

Reaction equation

HRID 541398 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[NH:16][C:17]([CH2:20][O:21][CH3:22])=[CH:18][N:19]=3)=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH3:23])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]2[C:14]([C:15]3[NH:16][C:17]([CH2:20][O:21][CH3:22])=[CH:18][N:19]=3)=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:23])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68288328methyl 4-cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoate2×

Product 1

HCID 682888074-Cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoate (compound 246.3, 150 mg, 0.430 mmol, 1.00 equiv, 90%) and aqueous sodium hydroxide (76.0 mg, 1.90 mmol, 4.00 equiv in 2 mL water) in methanol (4 mL) was stirred for 2 h at 60° C. After cooling to ambient temperature, the organic solvent was removed under reduced pressure. The pH value of the remaining aqueous phase was adjusted to −4 with hydrogen chloride (aq., 4 M). The resulting mixture was extracted with 2×50 mL of ethyl acetate, and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. This resulted in 120 mg (84%) of 4-cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoic acid as a white solid.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe resulting mixture was extracted with 2×50 mL of ethyl acetate
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThis resulted in 120 mg (84%) of 4-cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoic acid as a white solid

Sources & evidence

ORD record
ord-49208b356d2f46e1a443c98ac9a7330a
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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