Sodium Hydroxide → HCID 58508775, compound

HRID 454631Notes

Reaction equation

HRID 454631 reaction equation
[OH-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([NH:19][C:20]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:27]=[CH:26][C:21]=3[C:22]([O:24]C)=[O:23])=[O:18])=[C:15]([OH:38])[CH:14]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]>CO.O1CCOCC1>[C:3]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([NH:19][C:20]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:27]=[CH:26][C:21]=3[C:22]([OH:24])=[O:23])=[O:18])=[C:15]([OH:38])[CH:14]=2)[CH2:10][CH2:11]1)(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58508921HCID 58508921, compound

Product 1

HCID 58508775HCID 58508775, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.082 mL) was added to a solution mixture of the obtained methyl 2-(4-((1-acetylpiperidin-4-yl)oxy)-2-hydroxybenzamido)-4-phenylbenzoate (0.016 g) in methanol (0.5 mL) and dioxane (0.5 mL), followed by stirring at 60° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then methanol (1 mL), dioxane (1 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.082 mL) were added to the reaction mixture, followed by stirring at 60° C. for 3 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Water was added to the obtained residue, followed by adjusting the pH to 3 with 6 mol/L hydrochloric acid. The solid substance was collected from the reaction mixture by filtration to obtain 0.014 g of 2-(4-((1-acetylpiperidin-4-yl)oxy)-2-hydroxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 60° C. for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. additionWater was added to the obtained residue
  6. filtrationThe solid substance was collected from the reaction mixture by filtration

Sources & evidence

ORD record
ord-2fe6f9f63d5345209843d5a5fcbf4c82
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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