Sodium Hydroxide → HCID 178437949, compound

HRID 541303Notes

Reaction equation

HRID 541303 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][C:18]([CH2:20][CH3:21])=[N:17][N:16]=3)=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH2:22][CH3:23])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][C:18]([CH2:20][CH3:21])=[N:17][N:16]=3)=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:22][CH3:23])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178437951HCID 178437951, compound2×

Product 1

HCID 178437949HCID 178437949, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a round-bottom flask was added a solution of methyl 4-cyclobutyl-2-ethyl-5-(5-ethyl-4H-1,2,4-triazol-3-yl)benzoate (compound 181.8, 360 mg, 1.15 mmol, 1.00 equiv) in methanol (20 mL). A solution of sodium hydroxide (460 mg, 11.5 mmol, 10.0 equiv) in water (10 mL) was added to the reaction mixture. The resulting solution was stirred at 25° C. for 15 h. The organic solvent was then removed under reduced pressure. The pH value of the remaining aqueous phase was adjusted to 2-3 with hydrogen chloride (aq., 2 M). The resulting precipitate was collected by filtration and dried under high-vacuum to yield 320 mg (93%) of the title compound as a white solid.

Workup

  1. customThe organic solvent was then removed under reduced pressure
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried under high-vacuum

Sources & evidence

ORD record
ord-a128720a18784bcc8bec4838091cc51c
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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